Hydrochloric Acid → S-benzyl-(L)-cysteine methyl ester

HRID 1248272Notes

Reaction equation

HRID 1248272 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH:4]([N:14]=[N+]=[N-])[CH2:5][S:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl.[H][H]>CO.[Re]>[CH3:1][O:2][C:3](=[O:17])[C@H:4]([CH2:5][S:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:14]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14189838Methyl 2-azido-3-(benzylsulfanyl)propanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 450313S-benzyl-(L)-cysteine methyl esterYield 73.6%

Reagents, catalysts & solvents 2

HCID 23947RheniumCatalystHCID 887MethanolSolvent

Procedure

0.91 gram (3.62 mmoles) of the 2-azido-3-benzylmercapto-propionic acid methyl ester obtained in Example 4 was dissolved in 8 ml of methanol, treated with 0.27 gram (7.41 mmoles) of HCl gas and there was added 1 mole % of rhenium VII sulfide, based on the amount of azido compound employed. Hydrogen was led into this vigorously stirred reaction mixture for 45 hours. The working up according to Example 19 gave 0.60 gram (63% of theory) of S-benzyl-cysteine methyl ester.HCl having a melting point of 84° to 87° C.

Sources & evidence

ORD record
ord-f0a5c5ce686542189b28a8f6e09c99dc
Source dataset
uspto-grants-1985_06
Patent number
US04523012

Reaction notes

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