Phosphorus Oxychloride as an Efficient Coupling Reagent for the Synthesis of Ester, Amide and Peptide under Mild Conditions

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1 Supplementary Information for Phosphorus xychloride as an Efficient Coupling Reagent for the Synthesis of Ester, Amide and Peptide under Mild Conditions u Chen,* a,b Xunfu Xu, a Liu Liu, a Guo Tang,* a Yufen Zhao a a Department of Chemistry, College of Chemistry and Chemical Engineering, and the Key Laboratory for Chemical Biology of Fujian Province, Xiamen University, Xiamen, Fujian , China b Department of Chemistry and Chemical Engineering, efei Normal University, efei , China hchen808@yahoo.cn; t12g21@xmu.edu.cn Table of Contents Genera 2 Spectral Data 3-10 Copies of 1, 13 C, and PLC spectra

2 General: All reactions were carried out under N 2 atmosphere. All reagents were purchased and used without further purification. The solvent was freshly distilled. All new compounds were further characterized by RMS(ESI). Typical Procedure for Ester/Amide Synthesis. A solution of acid (0.5 mmol), alcohol or amine (0.6 mmol) and triethylamine (1.2 mmol) in anhydrous C 2 Cl 2 (1.5 ml) under N 2 atmosphere was added a solution of DMAP (0.15 mmol) in anhydrous C 2 Cl 2 (0.5 ml). After stirring for 5 min, PCl 3 (0.5 mmol) in anhydrous C 2 Cl 2 (1 ml) was added into the above reaction. After completion of reaction at room temperature (ca. 2 h, monitored through TLC), the reaction mixture was diluted with C 2 Cl 2 (30 ml). The organic phase was washed sequentially with ice-cooled water(10 ml), 10% aqueous Cl (10 ml), saturated aqueous NaC 3 solution (10 ml), and brine. Drying over anhydrous Na 2 S 4, removal of solvent under vacuum, and purification of the residue by silica gel column chromatography (petroleum ether/ethyl acetate 9/1~5/1) afforded the pure product. Synthesis of Dipeptide: A solution of the N-protected amino acid (0.5 mmol), methyl ester of amino acid hydrochloride (0.6 mmol) and triethylamine (1.8 mmol) in anhydrous C 2 Cl 2 (1.5 ml) under N 2 atmosphere was added a solution of 4-(dimethylamino) pyridine (0.15 mmol) in anhydrous C 2 Cl 2 (0.5 ml). After stirring for 5 min, the reaction mixture was added a solution of the PCl 3 (0.5 mmol) in anhydrous C 2 Cl 2 (1 ml), and stirring was continued at room temperature. After completion of reaction (ca. 2 h, TLC monitoring), the reaction mixture was diluted with C 2 Cl 2 (30 ml). The organic phase was washed sequentially with ice-cooled water(10 ml), 10% aqueous Cl (10 ml), saturated aqueous NaC 3 solution (10 ml), and brine. Drying over anhydrous Na 2 S 4, removal of solvent under vacuum, and purification of the residue by silica gel column chromatography (petroleum ether/ethyl acetate 9/1~5/1) afforded the pure product. Enantiomeric purity of the products formed was verified by PLC analysis. PLC conditions: column, CIRAL-CEL (D); mobile phase, 2~10% i-pr in n-hexane; flowrate, 1mL/min; UV detection at 225 nm. 2

3 Benzyl 3-phenylpropanoate (3a) (CAS no: ) 115 mg, 96% yield. 1 NMR (400 Mz, CDCl 3 ) δ (m, 7), (m, 3), 5.10 (s,2), 2.97 (t, J = 7.8 z, 2), 2.68 (t, J = 7.8 z, 2). 13 C NMR (100 Mz, CDCl 3 ) δ 172.7, 140.4, 135.9, 128.6, 128.5, 128.4, 128.3, 128.2, 126.2, 66.2, 35.9, ESI-MS: m/z ([M+] + ). Prop-2-yn-1-yl 3-phenylpropanoate (3b) (CAS no: ) 89 mg, 92% yield. 1 NMR (400 Mz, CDCl 3 ) δ (m, 2), (m, 3), 4.67 (d, J = 2.5 z, 2), 2.96 (t, J = 7.8 z, 2), (m, 2), 2.46 (t, J = 2.5 z, 1). 13 C NMR (100 Mz, CDCl 3 ) δ 171.9, 140.1, 128.5, 128.2, 126.3, 77.6, 74.8, 51.9, 35.5, ESI-MS: m/z ([M+] + ). Cinnamyl 3-phenylpropanoate (3c) (CAS no: ) 120 mg, 90% yield. 1 NMR (400 Mz, CDCl 3 ) δ (m, 2), (m, 5), (m, 3), 6.61 (d, J = 15.9 z, 1), 6.24 (dt, J = 15.9, 6.4 z, 1), 4.72 (dd, J = 6.5, 1.2 z, 2), 2.97 (t, J = 7.8 z, 2), 2.67 (dd, J = 9.3, 6.4 z, 2). 13 C NMR (100 Mz, CDCl 3 ) δ 172.6, 140.4, 136.1, 134.1, 128.6, 128.5, 128.3, 128.0, 126.6, 126.2, 123.1, 65.0, 35.9, ESI-MS: m/z ([M+] + ). (9-fluoren-9-yl)Methyl 3-phenylpropanoate (3d) 154 mg, 94% yield. IR (KBr, film), υ max (cm -1 ): 3063, 3027, 2948, 2359, 1736, 1450, 1291, 1250, 1159, 758, 740, 699; 1 NMR (400 Mz, CDCl 3 ) δ 7.74 (d, J = 7.6 z, 2), 7.52 (dd, J = 7.5, 0.7 z, 2), 7.38 (t, J = 7.3 z, 2), (m, 4), (m, 3), 4.38 (d, J = 7.1 z, 2), 4.16 (t, J = 7.1 z, 1), 2.95 (t, J = 7.8 z, 2), (m, 2). 13 C NMR (100 Mz, CDCl 3 ) δ 172.8, 143.7, 141.3, 140.4, 128.5, 128.2, 127.7, 127.1, 126.3, 125.0, 112.0, 66.3, 46.8, 35.9, RMS(ESI): m/z ([M+] +, C calcd ). Isopropyl 3-phenylpropanoate (3e) (CAS no: ) 3

4 90 mg, 94% yield. 1 NMR (400 Mz, CDCl 3 ) δ (m, 2), (m, 3), 5.00 (hept, J = 6.3 z, 1), 2.94 (t, J = 8.0 z, 2), 2.59 (t, J = 8.0 z, 2), 1.20 (d, J = 6.3 z, 6). 13 C NMR (100 Mz, CDCl 3 ) δ 172.4, 140.6, 128.4, 128.3, 126.1, 67.6, 36.2, 31.0, ESI-MS: m/z ([M+] + ). (1R, 2S, 5R)-2-Isopropyl-5-methylcyclohexyl 3-phenylpropanoate (3f) (CAS no: ) 137 mg, 95% yield. 1 NMR (400 Mz, CDCl 3 ) δ (m, 2), (m, 3), 4.67 (td, J = 10.9, 4.4 z, 1), (m, 2), 2.61 (dd, J = 8.6, 7.0 z, 2), (m, 1), (m, 1), (m, 2), (m, 1), (m, 1), (m, 1), (m, 1), (m, 3), (m, 4), 0.70 (d, J = 7.0 z, 3). 13 C NMR (100 Mz, CDCl 3 ) δ 172.5, 140.5, 128.4, 128.3, 126.2, 74.1, 46.9, 40.9, 36.2, 34.2, 31.3, 31.1, 26.1, 23.4, 22.0, 20.7, ESI-MS: m/z ([M+] + ). Phenyl 3-phenylpropanoate (3g) (CAS no: ) 103 mg, 91% yield. 1 NMR (400 Mz, CDCl 3 ) δ (m, 4), (m, 4), (m, 2), 3.07 (t, J = 7.7 z, 2), (m, 2). 13 C NMR (100 Mz, CDCl 3 ) δ 171.4, 150.6, 140.1, 129.4, 128.6, 128.4, 126.4, 125.8, 121.5, 35.9, ESI-MS: m/z 227.1([M+] + ). Naphthalen-1-yl 3-phenylpropanoate (3h) 121 mg, 88% yield. IR (KBr, film), υ max (cm -1 ): 3061, 3028, 2927, 1759, 1598, 1496, 1454, 1390, 1258, 1221, 1125, 794, 771, 698; 1 NMR (400 Mz, CDCl 3 ) δ (m, 1), 7.71 (d, J = 8.3 z, 1), 7.57 (dt, J = 8.5, 4.3 z, 1), (m, 3), (m, 5), 7.16 (dd, J = 7.5, 1.0 z, 1), (m, 2), (m, 2). 13 C NMR (100 Mz, CDCl 3 ) δ 171.4, 146.5, 140.1, 134.6, 128.7, 128.5, 127.9, 126.7, 126.5, 126.4, 126.3, 126.0, 125.3, 121.1, 118.0, 35.9, RMS(ESI): m/z ([M+] +, C calcd ). Benzyl cinnamate (3i) (CAS no: ) 4

5 107 mg, 90% yield. 1 NMR (400 Mz, CDCl 3 ) δ 7.73 (d, J = 16.0 z, 1), (m, 2), (m, 8), 6.48 (d, J = 16.0 z, 1), 5.25 (s, 2). 13 C NMR (100 Mz, CDCl 3 ) δ 166.8, 145.1, 136.0, 134.3, 130.3, 128.8, 128.6, 128.2, 128.2, 128.1, 117.8, ESI-MS: m/z 239.3([M+] + ). Benzyl cyclohexanecarboxylate (3j) (CAS no: ) 98 mg, 90% yield. 1 NMR (400 Mz, CDCl 3 ) δ (m, 5), 5.10 (s, 2), (m, 1), (m, 2), (m, 2), (m, 1), (m, 2), (m, 3). 13 C NMR (100 Mz, CDCl 3 ) δ 175.9, 136.3, 128.5, 128.0, 127.9, 65.8, 43.2, 28.9, 25.7, ESI-MS: m/z 219.2([M+] + ). Benzyl isonicotinate (3k) (CAS no: ) N 99 mg, 96% yield. 1 NMR (400 Mz, CDCl 3 ) δ 8.76 (dd, J = 4.4, 1.6 z, 2), 7.86 (dd, J = 4.4, 1.6 z, 2), (m, 5), 5.38 (s, 2). 13 C NMR (100 Mz, CDCl 3 ) δ 164.9, 150.5, 137.2, 135.2, 128.6, 128.5, 128.4, 128.3, 127.4, 126.9, 122.9, ESI-MS: m/z 214.0([M+] + ). Benzyl benzoate (3l) (CAS no: ) 95 mg, 90% yield. 1 NMR (400 Mz, CDCl 3 ) δ (m, 2), (m, 1), (m, 7), 5.36 (s, 2). 13 C NMR (100 Mz, CDCl 3 ) δ 166.4, 136.0, 133.0, 130.1, 129.7, 128.6, 128.3, 128.2, 128.1, ESI-MS: m/z 213.0([M+] + ). Benzyl 4-methylbenzoate (3m) (CAS no: ) 96 mg, 85% yield. 1 NMR (400 Mz, CDCl 3 ) δ (m, 2), (m, 2), (m, 3), (m, 2), 5.34 (s, 2), 2.39 (s, 3). 13 C NMR (100 Mz, CDCl 3 ) δ 166.5, 143.7, 136.1, 129.7, 129.0, 128.5, 128.1, 128.0, 127.3, 66.4, ESI-MS: m/z 227.1([M+] + ). Benzyl 2-nitrobenzoate (3n) (CAS no: ) 5

6 N mg, 96% yield. 1 NMR (400 Mz, CDCl 3 ) δ (m, 1), (m, 1), (m, 2), (m, 5), 5.35 (s, 2). 13 C NMR (100 Mz, CDCl 3 ) δ 165.2, 154.8, 148.1, 134.7, 132.9, 131.7, 129.8, 128.7, 128.6, 128.5, 127.5, 123.9, 89.7, ESI-MS: m/z 258.2([M+] + ). Dodecyl stearate (3o) (CAS no: ) mg, 90% yield. 1 NMR (400Mz, CDCl 3 ) δ 4.06 (t, J = 6.7z, 2), 2.30 (t, J = 7.5z, 2), 1.62 (t, J = 7.4z, 4), 1.26 (br s, 45), 0.89 (t, J = 6.8z, 6). 13 C NMR (100 Mz, CDCl 3 ) δ , 64.39, 34.41, 31.92, 29.70, 29.66, 29.63, 29.61, 29.57, 29.53, 29.48, 29.36, 29.35, 29.27, 29.25, 29.16, 28.65, 25.93, 25.03, 22.68, ESI-MS: m/z 453.4([M+] + ). ctadecyl stearate (3p) (CAS no: ) mg, 88% yield. 1 NMR (400Mz, CDCl 3 ) δ 4.05 (t, J = 5.7z, 2), 2.29 (t, J = 7.5z, 2), 1.63 (t, J = 6.8z, 4), 1.26 (br s, 58), 0.88 (t, J = 6.9z, 6). 13 C NMR (100 Mz, CDCl 3 ) δ , 64.40, 34.42, 31.92, 29.70, 29.65, 29.60, 29.58, 29.53, 29.48, 29.36, 29.27, 29.26, 29.16, 28.65, 25.94, 25.04, 22.69, ESI-MS: m/z 537.8([M+] + ). Cholest-5-en-3-ol (3β)-, 3-benzenepropanoate (3q) (CAS no: ) 197 mg, 76% yield. 1 NMR (400 Mz, CDCl 3 ) δ (m, 2), (m, 3), 5.29 (d, J = 4.0 z, 1), (m, 1), 2.87 (t, J = 7.8 z, 2), 2.52 (t, J = 7.8 z, 2), 2.21 (d, J = 7.8 z, 2), (m, 2), (m, 3), (m, 8), (m, 5), (m, 8), 0.94 (s, 3), 0.84 (d, J = 6.5 z, 3), 0.80 (d, J = 1.7 z, 3), 0.79 (d, J = 1.7 z, 3), 0.60 (s, 3). 13 C NMR (100 Mz, CDCl 3 ) δ 172.3, 140.6, 139.7, 128.4, 128.3, 126.2, 122.6, 74.0, 56.7, 56.2, 50.1, 42.3, 39.8, 39.5, 38.1, 37.0, 36.6, 36.3, 36.2, 35.8, 31.9, 31.8, 31.1, 28.2, 28.0, 27.8, 24.3, 23.8, 22.8, 22.5, 21.0, 19.3, 18.7, ESI-MS: m/z 519.4([M+] + ). N-Butyl-3-phenylpropanamide (5a) (CAS no: ) 6

7 97 mg, 95% yield. 1 NMR (400 Mz, CDCl 3 ) δ (m, 2), (m, 3), 5.39 (s, 1), 3.20 (td, J = 7.1, 5.8 z, 2), 2.96 (t, J = 8.0 z, 2), 2.45 (t, J = 8.0 z, 2), (m, 2), (m, 2), 0.88 (t, J = 7.3 z, 3). 13 C NMR (100 Mz, CDCl 3 ) δ 172.0, 140.9, 128.5, 128.3, 126.2, 39.2, 38.6, 31.8, 31.6, 19.9, ESI-MS: m/z 228.1([M+Na] + ). 3-Phenyl-1-(piperidin-1-yl)propan-1-one (5b) (CAS no: ) 95 mg, 88% yield. 1 NMR (400 Mz, CDCl 3 ) δ (m, 2), (m, 3), 3.55 (t, J = 5.6 z, 2), 3.32 (t, J = 5.6 z, 2), 2.96 (t, J = 8.0 z, 2), 2.61 (dd, J = 9.0, 7.0 z, 2), (m, 2), (m, 4). 13 C NMR (100 Mz, CDCl 3 ) δ 170.4, 141.4, 128.4, 128.3, 125.9, 46.5, 42.6, 35.0, 31.5, 26.3, 25.4, ESI-MS: m/z 240.2([M+Na] + ). N, N-Diallyl-3-phenylpropanamide (5c) (CAS no: ) 94 mg, 82% yield. 1 NMR (400 Mz, CDCl 3 ) δ (m, 2), (m, 3), (m, 2), (m, 4), 3.91 (d, J = 6.0 z, 2), 3.72 (dt, J = 4.6, 1.7 z, 2), 2.91 (t, J = 8.0 z,, 2), (m, 2). 13 C NMR (100 Mz, CDCl 3 ) δ 172.1, 141.3, 133.3, 132.8, 128.4, 126.0, 117.1, 116.5, 49.0, 47.9, 34.8, ESI-MS: m/z 252.0([M+Na] + ). N, 3-Diphenylpropanamide (5d) (CAS no: ) 101 mg, 90% yield. 1 NMR (400 Mz, CDCl 3 ) δ 7.55 (s, 1), 7.34 (d, J = 7.8 z, 2), (m, 4), (m, 3), 6.97 (t, J = 7.4 z, 1), 2.91 (t, J = 7.7 z, 2), 2.52 (t, J = 7.7 z, 2). 13 C NMR (100 Mz, CDCl 3 ) δ 170.7, 140.6, 137.8, 128.8, 128.5, 128.3, 126.3, 124.2, 120.1, 39.2, ESI-MS: m/z 248.1([M+Na] + ). N-(4-methoxyphenyl)-3-phenylpropanamide (5e) (CAS no: ) 117 mg, 92% yield. 1 NMR (400 Mz, CDCl 3 ) δ 7.29 (s, 1), (m, 4), (m, 3), 6.71 (dd, J = 12.0, 2.8 z, 2), 3.69 (s, 3), 2.93 (t, J = 7.7 z, 2), 2.52 (t, J = 7.7 z, 2). 13 C NMR (100 Mz, CDCl 3 ) δ 170.4, 156.4, 140.7, 130.9, 128.5, 128.3, 126.3, 122.0, 114.0, 55.4, 39.1, ESI-MS: m/z 278.0([M+Na] + ). 3-Phenyl-N-(o-tolyl)propanamide (5f) (CAS no: ) 7

8 104 mg, 87% yield. 1 NMR (400 Mz, CDCl 3 ) δ 7.59 (d, J = 7.9 z, 1), (m, 5), (m, 2), 6.96 (t, J = 7.3 z, 1), 6.88 (s, 1), 2.96 (t, J = 7.5 z, 2), 2.60 (t, J = 7.5 z, 2), 1.96 (s, 3). 13 C NMR (100 Mz, CDCl 3 ) δ 170.4, 140.5, 135.5, 130.4, 129.4, 128.6, 128.4, 126.6, 126.4, 125.2, 123.4, 39.1, 31.7, ESI-MS: m/z 262.0([M+Na] + ). N-Butylbenzamide (5g) (CAS no: ) N Bu-n 84 mg, 95% yield. 1 NMR (400 Mz, CDCl 3 ) δ (m, 2), (m, 1), (m, 2), 6.44 (s, 1), 3.34 (dd, J = 13.5, 6.6 z, 2), (m, 2), (m, 2), 0.85 (t, J = 7.3 z, 3). 13 C NMR (100 Mz, CDCl 3 ) δ 167.6, 134.8, 131.1, 128.4, 126.8, 39.7, 31.6, 20.1, ESI-MS: m/z 200.2([M+Na] + ). N-Butyl-4-methylbenzamide (5h) (CAS no: ) 88 mg, 92% yield. 1 NMR (400 Mz, CDCl 3 ) δ (m, 2), 7.11 (d, J = 7.9 z, 2), 6.32 (s, 1), 3.34 (td, J = 7.2, 5.8 z, 2), 2.29 (s, 3), (m, 2), (m, 2), 0.86 (t, J = 7.3 z, 3). 13 C NMR (100 Mz, CDCl 3 ) δ 167.5, 141.5, 131.9, 129.0, 126.8, 39.7, 31.7, 21.3, 20.1, ESI-MS: m/z 214.1([M+Na] + ). N-Butyl-4-ethoxybenzamide (5i) (CAS no: ) 93 mg, 84% yield. 1 NMR (400 Mz, CDCl 3 ) δ (m, 2), (m, 2), 5.99 (s, 1), 4.00 (q, J = 7.0 z, 2), 3.36 (td, J = 7.1, 5.8 z, 2), (m, 2), (m, 5), (m, 3). 13 C NMR (100 Mz, CDCl 3 ) δ 167.1, 161.5, 128.6, 127.0, 114.2, 63.6, 39.7, 31.8, 20.2, 14.7, ESI-MS: m/z 244.2([M+Na] + ). N-Butyl-4-chlorobenzamide (5j) (CAS no: ) 101 mg, 96% yield. 1 NMR (400 Mz, CDCl 3 ) δ 7.62 (d, J = 8.5 z, 2), 7.28 (d, J = 8.5 z, 2), 6.43 (s, 1), 3.33 (dd, J = 13.2, 6.9 z, 2), (m, 2), (m, 2), 0.86 (t, J = 7.3 z, 3). 13 C NMR (100 Mz, CDCl 3 ) δ 166.5, 137.4, 133.2, 128.6, 128.3, 39.9, 31.6, 20.1, ESI-MS: m/z 244.2([M+Na] + ). ESI-MS: m/z 234.1([M+Na] + ). 8

9 N-Butyl-4-nitrobenzamide (5k) (CAS no: ) 107 mg, 96% yield. 1 NMR (400 Mz, CDCl 3 ) δ (m, 2), (m, 2), 6.46 (s, 1), 3.39 (td, J = 7.2, 5.8 z, 2), (m, 2), (m, 2), 0.88 (t, J = 7.3 z, 3). 13 C NMR (100 Mz, CDCl 3 ) δ 165.5, 149.4, 140.4, 128.1, 123.7, 40.1, 31.5, 20.1, ESI-MS: m/z 245.3([M+Na] + ). Cbz-Phe-Leu-Me (5l) (CAS no: ) 203 mg, 95% yield. 1 NMR (400 Mz, CDCl 3 ) δ (m, 5), (m, 3), (m, 2), 6.30 (d, J = 7.6 z, 1), 5.39 (d, J = 7.6 z, 1), 5.08 (s, 2), (m, 1), (m, 1), 3.69 (s, 3), (m, 2), (m, 3), 0.88 (t, J = 6.2 z, 6). 13 C NMR (100 Mz, CDCl 3 ) δ 172.8, 170.6, 155.9, 136.2, 136.0, 129.3, 128.6, 128.5, 128.2, 128.0, 127.0, 67.0, 55.9, 52.2, 50.7, 41.4, 38.3, 24.6, 22.6, 21.8; ESI-MS: m/z 449.2([M+Na] + ). PLC retention time = 12.0 min (mobile phase, 7% i-pr in n-hexane). Cbz-Ala-Ala-Me (5m), (CAS no: ) 145 mg, 94% yield. 1 NMR (400 Mz, CDCl 3 ) δ (m, 5), 6.79 (d, J = 6.3 z, 1), 5.56 (d, J = 7.4 z, 1), (m, 2), 4.56 (p, J = 7.2 z, 1), (m, 1), 3.74 (s, 3), 1.38 (d, J = 7.0 z, 6). 13 C NMR (100 Mz, CDCl 3 ) δ 173.1, 171.9, 155.9, 136.1, 128.5, 128.1, 128.0, 66.9, 52.4, 50.3, 48.0, 18.7, ESI-MS: m/z 331.1([M+Na] + ). PLC retention time = 15.8 min (mobile phase, 10% i-pr in n-hexane). Boc-Ile-Val-Me (5n) (CAS no: ) 143 mg, 83% yield. 1 NMR (400 Mz, CDCl 3 ) δ 6.45 (d, J = 8.3 z, 1), 5.11 (d, J = 8.6 z, 1), 4.55 (dd, J = 8.7, 4.9 z, 1), 3.96 (dd, J = 16.6, 8.7 z, 1), 3.74 (s, 3), (m, 1), (m, 1), (m, 1), 1.44 (s, 9), (m, 1), (m, 12). 13 C NMR (100 Mz, CDCl 3 ) δ 172.1, 171.6, 155.7, 79.8, 59.3, 57.0, 52.1, 36.9, 31.2, 28.2, 24.7, 18.9, 17.7, 15.4, ESI-MS: m/z 367.4([M+Na] + ). PLC retention time = 10.4 min (mobile phase, 2% i-pr in n-hexane). Boc-Val-Val-Me (5o) (CAS no: ) 9

10 159 mg, 96% yield. 1 NMR (400 Mz, CDCl 3 ) δ 6.47 (d, J = 8.1 z, 1), 5.12 (d, J = 8.6 z, 1), 4.55 (dd, J = 8.7, 4.9 z, 1), 3.93 (dd, J = 10.6, 4.6 z, 1), 3.74 (s, 3), (m, 2), 1.45 (s, 9), (m, 12). 13 C NMR (100 Mz, CDCl 3 ) δ 172.1, 171.9, 171.6, 162.9, 155.8, 79.8, 60.1, 57.0, 52.1, 31.1, 30.6, 28.2, 19.2, 18.9, 17.9, ESI-MS: m/z 353.2([M+Na] + ). PLC retention time = 6.6 min (mobile phase, 2% i-pr in n-hexane). Boc-Phe-Gly-Et (5p) (CAS no: ) N Boc Ph N CC mg, 91% yield. 1 -NMR (400 Mz, CDCl 3 ) δ(ppm) 1.27 (t, J = 7.1 z, 3), 1.39 (s, 9), 3.05 (m, 1), 3.13 (dd, J = 6.5, 13.9 z, 1), 3.92 (dd, J = 4.9, 18.3 z, 1), 4.02 (dd, J = 5.4, 18.2 z, 1), 4.19 (q, J=7.1 z, 2), 4.43 (d, J = 6.2 z, 1), 5.11 (br d, J = 7.2 z, 1), 6.57 (t, J = 5.0 z, 1), (m,5) ; 13 C-NMR (100 Mz, CDCl 3 ) δ(ppm) 171.5, 169.4, 155.4, 136.6, 129.2, 128.6, 126.9, 80.2, 61.5, 55.5, 41.3, 38.3, 28.2, 14.1, 1.0; ESI-MS: m/z ([M+Na] + ); PLC retention time = 13.6 min (mobile phase, 7% i-pr in n-hexane); Boc-Phe-Ala-Me (5q) (CAS no: ) 159 mg, 91% yield. 1 -NMR (400 Mz, CDCl 3 ) δ(ppm) 1.35 (d, J = 7.2 z, 3), 1.40 (s, 9), 3.07 (d, J = 6.5 z, 2), 3.71 (s, 3), 4.39 (d, J = 6.2 z, 1), 4.52 (p, J = 7.1 z, 1), 5.08 (br d, J = 5.9 z, 1), 6.55 (br d, J = 5.6 z, 1 ), (m,5); 13 C-NMR (100 Mz, CDCl 3 ) δ(ppm) 172.8, 170.8, 155.3, 136.5, 129.3, 128.6, 126.9, 80.1, 55.5, 52.4, 48.0, 38.3, 28.2, 18.3; ESI-MS: m/z: 373.2([M+Na] + ); PLC retention time = 11.7 min (mobile phase, 7% i-pr in n-hexane); Boc-Val-Leu-Me (5r) (CAS no: ) 151 mg, 88% yield. 1 -NMR (400 Mz, CDCl 3 ) δ(ppm) (m, 12), 1.44 (s, ), (m, 1), (m, 1), (m, 1), 3.73 (s, 3), 3.92 (dd, J = 6.8, 8.6 z, 1), (m, 1), 5.13 (br d, J = 8.8, 1 ), 6.41 (br d, J = 7.8z, 1); 13 C-NMR (100 Mz, CDCl 3 ) δ(ppm) 173.1, 171.5, 155.8, 79.8, 59.8, 52.2, 50.6, 41.3, 30.8, 28.2, 24.7, 22.7, 21.8, 19.1, 17.8; ESI-MS: m/z 367.3([M+Na] + ); PLC retention time = 10.3 min (mobile phase, 2% i-pr in n-hexane). 10

11 3a 11

12 3b 12

13 3c 13

14 3d 14

15 3e 15

16 3f 16

17 3g 17

18 3h 18

19 3i 19

20 3j 20

21 3k 21

22 3l 22

23 3m 23

24 3n 24

25 3o

26 3p

27 3q 27

28 5a 28

29 5b 29

30 5c 30

31 5d 31

32 5e 32

33 5f Ph N Ph N 33

34 5g 34

35 5h 35

36 5i 36

37 5j 37

38 5k 38

39 5l PEAK# RT(min) AREA AREA% PEAK# RT(min) AREA AREA%

40 5m Cbz N N CC 3 PEAK# RT(min) AREA AREA% PEAK# RT(min) AREA AREA%

41 5n PEAK# RT(min) AREA AREA% PEAK# RT(min) AREA AREA%

42 5o PEAK# RT(min) AREA AREA% PEAK# RT(min) AREA AREA%

43 5p Ph N Boc N CC 2 5 Ph N Boc N CC 2 5 Ph N Boc N CC 2 5 Ph N Boc N CC 2 5 PEAK# RT(min) AREA AREA% PEAK# RT(min) AREA AREA%

44 5q Ph N Boc N CC 3 Ph N Boc N CC 3 Ph N Boc N CC 3 Ph N Boc N CC 3 PEAK# RT(min) AREA AREA% PEAK# RT(min) AREA AREA%

45 5r Boc N N CC 3 Boc N N CC 3 Boc N N CC 3 Boc N N CC 3 PEAK# RT(min) AREA AREA% PEAK# RT(min) AREA AREA%

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