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

HRID 346174Notes

Reaction equation

HRID 346174 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 (5.0g) 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 (4.31g), 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-c1ebb8bc4ac742f783688ed9cd9cb4cb
Source dataset
uspto-grants-1991_10
Patent number
US05061710

Reaction notes

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