Ethanol → (4S)-4-(4-cyclohexylbenzylthio)-L-proline

HRID 1066202ノート

反応式

HRID 1066202 の反応式
Cl.[SH:2][C@@H:3]1[CH2:7][NH:6][C@H:5]([C:8]([OH:10])=[O:9])[CH2:4]1.[OH-].[Na+].[CH:13]1([C:19]2[CH:26]=[CH:25][C:22]([CH2:23]Cl)=[CH:21][CH:20]=2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.C(O)C>C(Cl)(Cl)Cl>[CH:13]1([C:19]2[CH:26]=[CH:25][C:22]([CH2:23][S:2][C@@H:3]3[CH2:7][NH:6][C@H:5]([C:8]([OH:10])=[O:9])[CH2:4]3)=[CH:21][CH:20]=2)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1

参加物

6

反応物 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 133433651-(Chloromethyl)-4-cyclohexylbenzeneHCID 74890044(4S)-4-mercapto-L-proline hydrochloride

生成物 1

HCID 68543958(4S)-4-(4-cyclohexylbenzylthio)-L-proline収率 91%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
0 °C

実験手順

To (4S)-4-mercapto-L-proline hydrochloride (300 mg) is added 2 N sodium hydroxide (1.6 ml) aqueous solution, and the mixture is stirred at 0° C. A solution of 4-cyclohexylbenzyl chloride (340 mg) in a mixed solvent of ethanol (5 ml)/chloroform (1 ml) is added thereto, and the mixture is stirred at room temperature overnight. The reaction mixture is concentrated under reduced pressure, and deposited crystals are filtered off. The crystals are washed with water, ethanol and diethyl ether successively to give 470 mg (91%) of the titled compound.

後処理

  1. stirringthe mixture is stirred at room temperature overnight
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. filtrationare filtered off
  4. washThe crystals are washed with water, ethanol and diethyl ether successively

出典と根拠

ORDレコード
ord-2d30957efc5a4950a439d40b694b9fb3
出典データセット
uspto-grants-2001_06
特許番号
US06242476B1

反応ノート

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