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

HRID 842356Notes

Reaction equation

HRID 842356 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].C(=O)([O-])[O-].[Na+].[Na+].[C:24]1([SH:30])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.Cl>O>[C:1]([NH:11][C@H:12]([C:15]([OH:17])=[O:16])[CH2:13][S:30][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=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 10340Sodium CarbonateHCID 11043414N-carbobenzyloxy-beta-chloro-L-alanine

Product 1

HCID 2733947(R)-2-(((Benzyloxy)carbonyl)amino)-3-(phenylthio)propanoic acidYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

N-Carbobenzyloxy-β-chloro-L-alanine (0.108 g, 0.42 mmol) was dissolved in 0.5 ml of water and, then, 0.097 g (0.92 mmol) of sodium carbonate was added. Thereafter, 0.054 g (0.50 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 0.112 g (0.34 mmol, 81%) of N-carbobenzyloxy-S-phenyl-L-cysteine. The compound obtained had an optical purity of not less than 98% e.e. The optical purity was determined by HPLC. The analytical conditions are shown below.

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-674346be4a48436f87b5216d1c259f9a
Source dataset
uspto-grants-2002_04
Patent number
US06372941B1

Reaction notes

Loading…