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Toluene → {2-Phenyl-4-[(thiazol-2-ylamino)carbonylthio]benzoyl}-methionine methyl ester

HRID 383097
ノート
印刷プレビュー

反応式

HRID 383097 の反応式
[CH3:1][O:2][C:3](=[O:25])[C@H:4]([CH2:21][CH2:22][S:23][CH3:24])[NH:5][C:6](=[O:20])[C:7]1[CH:12]=[CH:11][C:10]([SH:13])=[CH:9][C:8]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[C:26](Cl)(Cl)=[O:27].C1(C)C=CC=CC=1.[NH2:37][C:38]1[S:39][CH:40]=[CH:41][N:42]=1.C(N(CC)CC)C>C(Cl)Cl.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:25])[C@H:4]([CH2:21][CH2:22][S:23][CH3:24])[NH:5][C:6](=[O:20])[C:7]1[CH:12]=[CH:11][C:10]([S:13][C:26]([NH:37][C:38]2[S:39][CH:40]=[CH:41][N:42]=2)=[O:27])=[CH:9][C:8]=1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 5

HCID 1140TolueneHCID 21552-AminothiazoleHCID 6371PhosgeneHCID 8471TriethylamineHCID 542379062-Phenyl4-mercaptobenzoyl-methionine methyl ester

生成物 1

HCID 86586788{2-Phenyl-4-[(thiazol-2-ylamino)carbonylthio]benzoyl}-methionine methyl ester

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒
HCID 6344Dichloromethane溶媒2 回
HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 2-phenyl-4-mercaptobenzoyl-methionine methyl ester from example 12E or 12F (1 equivalent) in methylene chloride is added a solution of phosgene in toluene (1.0 equivalent) and p-dimethylaminopyridine (2.0 equivalents). When the reaction is judged complete by TLC analysis, the solvent is evaporated with toluene chasers. The thiochloroformate is reacted without further purification with 2-aminothiazol (1.0 equivalent) and triethylamine (1.0 equivalent) in dichloromethane. When judged complete by TLC analysis, the reaction is taken up in ethyl acetate and washed with 1N HCl and brine, evaporated, and purified by chromatography on silica gel.

後処理

  1. customthe solvent is evaporated with toluene chasers
  2. washwashed with 1N HCl and brine
  3. customevaporated
  4. custompurified by chromatography on silica gel

出典と根拠

ORDレコード
ord-6fdb69240f6c4a84ab7827dee89c96fe
出典データセット
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06310095B1

反応ノート

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