Acetic Anhydride → N-acetyl-S-phenyl-cysteine methyl ester

HRID 1248273Notes

Reaction equation

HRID 1248273 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH:4]([N:13]=[N+]=[N-])[CH2:5][S:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[H][H].[C:19](OC(=O)C)(=[O:21])[CH3:20]>[Re]>[CH3:1][O:2][C:3](=[O:16])[C@H:4]([CH2:5][S:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[NH:13][C:19](=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 13192751Methyl 2-azido-3-(phenylsulfanyl)propanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 2723737N-acetyl-S-phenyl-cysteine methyl esterYield 47%

Reagents, catalysts & solvents 1

HCID 23947RheniumCatalyst

Procedure

1.00 gram (4.22 mmoles) of the 2-azido-3-phenylmercapto-propionic acid methyl ester obtained in Example 2 was dissolved in 5 ml of acetic anhydride and then was added 1 mole % of rhenium VII sulfide based on the azido compound employed. Under vigorous stirring there was led hydrogen through the solution for 24 hours at 70° C. After the end of the reaction the solvent was drawn off under reduced pressure on the rotary evaporator, the product taken up in diethyl ether and the catalyst filtered off. Chromatography on a silica gel column with petroleum ether/ethyl acetate (volume ratio 1:1) gave 0.50 gram (47% of theory) of N-acetyl-S-phenyl-cysteine methyl ester as a colorless oil.

Workup

  1. customfor 24 hours
  2. customat 70° C
  3. customAfter the end of the reaction the solvent
  4. customwas drawn off under reduced pressure on the rotary evaporator
  5. filtrationthe catalyst filtered off

Sources & evidence

ORD record
ord-f88ad15267f144d6b15771338be731ea
Source dataset
uspto-grants-1985_06
Patent number
US04523012

Reaction notes

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