Hydrochloric Acid → (R)-2-(((Benzyloxy)carbonyl)amino)-3-(phenylthio)propanoic acid

HRID 842358Notes

Reaction equation

HRID 842358 reaction equation
[C:1]([NH:11][C@H:12]([C:15]([OH:17])=[O:16])[CH2:13]Cl)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[OH-].[Na+].[C:20]1([SH:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl>O>[C:1]([NH:11][C@H:12]([C:15]([OH:17])=[O:16])[CH2:13][S:26][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7969ThiophenolHCID 14798Sodium HydroxideHCID 11043414N-carbobenzyloxy-beta-chloro-L-alanine

Product 1

HCID 2733947(R)-2-(((Benzyloxy)carbonyl)amino)-3-(phenylthio)propanoic acidYield 61%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

N-Carbobenzyloxy-β-chloro-L-alanine (0.137 g, 0.53 mmol) was dissolved in 0.68 ml of water and, then, 0.58 ml of 2 N aqueous sodium hydroxide was added. Thereafter, 0.069 g (0.63 mmol) of thiophenol was added dropwise at room temperature in a nitrogen gas atmosphere. After 2 hours of stirring at 60° C., the reaction mixture was cooled with ice and acidified with 1 N hydrochloric acid, and then extracted with ethyl acetate. The solvent was distilled off and the residue was purified by column chromatography to give 0.107 g (0.32 mmol, 61%) of N-carbobenzyloxy-S-phenyl-L-cysteine. The product obtained had an optical purity of not less than 98% e.e. as determined by HPLC analysis in the same manner as in Example 13.

Workup

  1. temperaturethe reaction mixture was cooled with ice
  2. extractionextracted with ethyl acetate
  3. distillationThe solvent was distilled off
  4. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-2be2d686f94c42bc82c1b2c17374a2e3
Source dataset
uspto-grants-2002_04
Patent number
US06372941B1

Reaction notes

Loading…