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

HRID 257529ノート

反応式

HRID 257529 の反応式
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

参加物

4

反応物 3

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

生成物 1

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

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-819f6675241444b2835bdf41dfb5db87
出典データセット
uspto-grants-1993_11
特許番号
US05262436

反応ノート

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