Diazomethane → L-Cysteine, N-acetyl-, methyl ester

HRID 2231729Notes

Reaction equation

HRID 2231729 reaction equation
[C:1]([NH:4][C@H:5]([C:8]([OH:10])=[O:9])[CH2:6][SH:7])(=[O:3])[CH3:2].[N+](=[CH2:13])=[N-]>CCOCC>[CH3:13][O:9][C:8](=[O:10])[C@H:5]([CH2:6][SH:7])[NH:4][C:1](=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 12035N-Acetyl-L-Cysteine

Product 1

HCID 6542158L-Cysteine, N-acetyl-, methyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

N-Acetyl-L-cysteine (5 g, 30.6 mM) was treated with excess diazomethane (generated from N-nitrosomethyl urea) in ether for 6 hr at RT. Unreacted starting material was removed by filtration and the resulting yellow filtrate was allowed to stand overnight. The solvent was removed in vacuo and the residue crystallized from Et2O/Pet. ether to give pure N-acetyl-L-cysteine methyl ester (650 mg); mp 73°-76° C. compared to a literature mp of 81°-82° C. in the Journal of Organic Chemistry, Vol. 35, p. 3542 (1970) and 79°-80° C. in the Canadian Jounral of Chemistry, Vol. 44, p. 2517 (1966).

Workup

  1. customwas removed by filtration
  2. customThe solvent was removed in vacuo
  3. customthe residue crystallized from Et2O/Pet. ether

Sources & evidence

ORD record
ord-2061196996844e3aa4c9980613bad038
Source dataset
uspto-grants-1988_11
Patent number
US04783483

Reaction notes

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