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

HRID 1066202Notes

Reaction equation

HRID 1066202 reaction equation
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

Participants

6

Reactant 4

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

Product 1

HCID 68543958(4S)-4-(4-cyclohexylbenzylthio)-L-prolineYield 91%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2d30957efc5a4950a439d40b694b9fb3
Source dataset
uspto-grants-2001_06
Patent number
US06242476B1

Reaction notes

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