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

HRID 341759

反応式

HRID 341759 の反応式
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]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 60960Cysteine Hydrochloride

生成物 1

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

試薬・触媒・溶媒 1

HCID 14798Sodium Hydroxide溶媒2 回

反応条件

温度
0 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-1360925152c1482681108626c9474932
出典データセット
uspto-grants-1999_01
特許番号
US05856310

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