(S)-1-N-Cbz-prolinamide ...
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(S)-1-N-Cbz-prolinamide ...
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CAS No:
34079-31-7
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Formula:
C13H16N2O3
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Chemical Name:
(S)-1-N-Cbz-prolinamide ...
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CAS No:
(S)-1-N-Cbz-prolinamide ... Use and Manufacturing
To a solution of starting 1-{[(phenylmethyl)oxy]carbonyl}-L-proline (8.0 g, 32.09 mmol), pyridine (1.5 mL), (BoC)Step A - Syntheses of Intermediate Compound Int-13b (0313) (0314) Ethyl chloroformate (12 mL, 125 mmol) in 180 mL of THF was added drop-wise to a cooled solution (-5°C) of compound Z-Pro-OH (13.8 g, 55.5 mmol), TEA (7.71 mL, 55.5 mmol). The resulting slurry was allowed to stir for 20 minutes at -5°C before saturated NHThe obtained N-benzyloxycarbonyl-L-prolyl chloride was stirred under cooling to 0 ~ 10 ° C, the temperature was controlled to 10 ~ 20 ° C, and ammonia gas was passed for 12 hours. After completion of the reaction, the resulting mixture was concentrated to dryness under reduced pressure. 100 kg dichloromethane was added, stirred to dissolve, cooled to 0 ~ 5 ° C, the temperature was controlled to 10 ~ 15 ° C, 30percent sodium hydroxide was added to adjust pH to 12 ~ 13, stirred at 10 ~ 15 ° C for 1 hour. pH was retested, the mixture was allowed to stand, liquid separation was carried out, aqueous layer was separated, 10 kg activated carbon was added to dichloromethane layer, stirred at 20-25° C for 40 minutes, filtered, and the resulting dichloromethane solution was washed twice with 200 kg of purified water, 30 kg anhydrous magnesium sulfate was added to dichloromethane layer, dehydrated, filtered, dichloromethane was distilled off, cooled to 5 ~ 10 ° C, 500 kg petroleum ether was added, solids were precipitated, stirred at 5 ~ 10 ° C for 8 hours, filtered, washed with 50 kg petroleum ether and dried to get 177 kg white solid. Yield 82.0percent, purity 99.8percent, optical purity of 99.9percent (HPLC area normalization method)
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