N-Acetyl-L-Cysteine → N-acetyl-S-benzamidomethyl-L-cysteine

HRID 325847Notes

Reaction equation

HRID 325847 reaction equation
[C:1]([NH:4][C@H:5]([C:8]([OH:10])=[O:9])[CH2:6][SH:7])(=[O:3])[CH3:2].ClC[C:13]1[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15]([NH2:17])=[O:16].O1CCOC[CH2:23]1>>[C:1]([NH:4][C@H:5]([C:8]([OH:10])=[O:9])[CH2:6][S:7][CH2:23][NH:17][C:15](=[O:16])[C:14]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:13]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 12035N-Acetyl-L-CysteineHCID 312751,4-DioxaneHCID 222911382-(Chloromethyl)benzamide

Product 1

HCID 56623287N-acetyl-S-benzamidomethyl-L-cysteine

Conditions

Temperature
25 °C

Procedure

N-acetyl-L-cysteine (0.5 g, 3.06 mmol) was dissolved in 50 ml of dry dioxane. Chloromethyl benzamide (0.52 g, 3.06 mmol) was added and the colorless solution was stirred at 25° C. for 18 hours. The dioxane was evaporated under vacuum with minimal amount of heating to give a colorless oil: NMR (CDCl3 +DMSO) δ8.05-7.38 (m, 5, aryl), 4.58 (d, 2, --SCH2NH--), 2.01 (s, 3, --CH3).

Workup

  1. customThe dioxane was evaporated under vacuum with minimal amount
  2. temperatureof heating
  3. customto give a colorless oil

Sources & evidence

ORD record
ord-4e22385d2bb6471cae26836b3ae457d4
Source dataset
uspto-grants-1984_04
Patent number
US04443435

Reaction notes

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