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

HRID 842357Notes

Reaction equation

HRID 842357 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+].[C:23]1([SH:29])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.Cl>O>[C:1]([NH:11][C@H:12]([C:15]([OH:17])=[O:16])[CH2:13][S:29][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=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 516892Sodium BicarbonateHCID 11043414N-carbobenzyloxy-beta-chloro-L-alanine

Product 1

HCID 2733947(R)-2-(((Benzyloxy)carbonyl)amino)-3-(phenylthio)propanoic acidYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

N-Carbobenzyloxy-β-chloro-L-alanine (0.091 g, 0.35 mmol) was dissolved in 0.45 ml of water and, then, 0.065 g (0.77 mmol) of sodium hydrogen carbonate was added. Thereafter, 0.046 g (0.42 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 0.097 g (0.29mmol, 84%) 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 following the same procedure 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-08b7ea5c319d4a1a91392e51235b2cd4
Source dataset
uspto-grants-2002_04
Patent number
US06372941B1

Reaction notes

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