Methanol → S-(4-Methylbenzyl)-L-Cysteine, Methyl Ester, Hydrochloride

HRID 257529Notes

Reaction equation

HRID 257529 reaction equation
S(Cl)([Cl:3])=O.C(OC([NH:12][C@H:13]([C:24]([OH:26])=[O:25])[CH2:14][S:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1)=O)(C)(C)C.[CH3:27]O>>[ClH:3].[CH3:23][C:20]1[CH:19]=[CH:18][C:17]([CH2:16][S:15][CH2:14][C@@H:13]([C:24]([O:26][CH3:27])=[O:25])[NH2:12])=[CH:22][CH:21]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 7010551N-alpha-t-Butyloxycarbonyl-S-(4-methyl-benzyl)-L-cysteine

Product 1

HCID 14390657S-(4-Methylbenzyl)-L-Cysteine, Methyl Ester, Hydrochloride

Procedure

At room temperature, add thionyl chloride (2.8 ml, 2.2 equiv.) dropwise to N-t-butyloxycarbonyl-S-(4-methylbenzyl)-L-cysteine (5.0 g) in methanol (500 ml) and heat the resulting mixture under reflux for 90 minutes. Cool the reaction mixture to room temperature and concentrate in vacuo to give the title compound, a white solid (4.31 g), m.p. 158°-160°, [α]D26 =-22.9° (MeOH).

Workup

  1. temperatureheat the resulting mixture
  2. temperatureunder reflux for 90 minutes
  3. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-819f6675241444b2835bdf41dfb5db87
Source dataset
uspto-grants-1993_11
Patent number
US05262436

Reaction notes

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