Synthesis of N-(Tert-butoxycarbonyl)-3-(4-thiazoIyl)-L-alanine

References

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• Both enzymes were purchased from Sigma Chemical Company . Subtilisin Carisberg, catalog No. p 5380; Chymotrypsin, type I-S, from bovine pancreas, catalog No. c 7762
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• The enantiomeric excess of 11 was determined to be >99% by HPLC analysis of the corresponding 3,4-dimethylanilide prepared via the standard condition (11/HOBT/EDAC/3,4-dimethylaniline/CH2Cl2/0°C). Column; L-Leucine Covalent, 25 cm × 4.6 mm (from Regis Chemical Company, catalog No. 731041W); eluent, hexane/2-propanol (90/10) mixture; flow rate, 2.00 mL/min; tR of the D-enantiomer, 7.93 min; tR of the L-enantiomer, 9.34 min
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• 19 was desalted by ion exchange column (Dowex 50W-X8, 100–200 mesh, H+ form) to obtain analytically pure 2 as an off white solid: mp 236–238°C; 1H NMR (300 MHz, D2O) δ 3.35 (dd, J =15 Hz, J = 7.5 Hz, 1H), 3.47 (dd, J = 15 Hz, J = 6 Hz, 1H), 4.10 (dd, J = 7.5 Hz, J = 6 Hz, 1H), 7.43 (d, J =1.5 Hz, 1H), 9.00 (d, J = 1.5 Hz, 1H); [ α]D-31.6° (c 1.20, H2O). Anal. Calcd for C6H8N2O2S: C, 41.85; H, 4.68; N, 16.27; S, 18.62. Found: C, 41.74; H, 4.78; N, 16.05; S, 18.43
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