Hydrochloric Acid → N,S-Bis[(phenylmethoxy)carbonyl]-L-cysteine

HRID 341759

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HRID 341759 반응식
Cl.[NH2:2][C@H:3]([C:6]([OH:8])=[O:7])[CH2:4][SH:5].Cl[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].Cl>[OH-].[Na+]>[C:10]([NH:2][C@H:3]([C:6]([OH:8])=[O:7])[CH2:4][S:5][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 60960Cysteine Hydrochloride

생성물 1

HCID 7021869N,S-Bis[(phenylmethoxy)carbonyl]-L-cysteine수율 80%

시약·촉매·용매 1

HCID 14798Sodium Hydroxide용매2회

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온도
0 °C

실험 절차

Cysteine HCl (2.0 g, 12.6 mmol) was dissolved in 2N NaOH and benzyl chloroformate (4.5 mL) was slowly added over 15 min. The pH value of the solution was kept at 9-10 by addition of 2 N NaOH (~7 mL) at 0° C. After vigorous stirring for 1 h at 0° C., the aqueous solution was acidified with 2N HCl at pH ~2 to form a colorless syrup. The aqueous solution was decanted and the sticky syrup was triturated with petroleum ether (100 ml×3) to give N,S-diCBZ-cysteine (3.94 g, 80%) as a white solid. Analytically pure sample could also be obtained by flash chromatography (on silica gel, 5% CH3OH in EtOAc):mp.93°-94° C.; 1H NMR (CDCl3) δ7.33 (10H, m), 5.67 (1H, d, J=7.7 Hz), 5.21 (2H, s), 5.12 (2H, s), 4.66 (1H, ddd, J=7.7, 6.7, 4.4 Hz), 3.31 (1H, dd, J=6.7, 14.5 Hz).

후처리

  1. customto form a colorless syrup
  2. customThe aqueous solution was decanted
  3. customthe sticky syrup was triturated with petroleum ether (100 ml×3)

출처 및 근거

ORD 기록
ord-1360925152c1482681108626c9474932
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05856310

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