Triethylamine → 7beta-Phenoxyacetylamino-3-methanesulphonyloxy-2-cephem-4-carboxylic acid diphenylmethyl ester

HRID 127648ノート

反応式

HRID 127648 の反応式
[C:1]1([CH:7]([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:36])[C@@H:24]([NH:25][C:26](=[O:35])[CH2:27][O:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[C@H:21]3[S:20][CH2:19][C:18]=2[OH:37])=[O:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:38][S:39](Cl)(=[O:41])=[O:40].C(N(CC)CC)C>C(Cl)Cl>[C:1]1([CH:7]([O:14][C:15]([CH:17]2[N:22]3[C:23](=[O:36])[C@@H:24]([NH:25][C:26](=[O:35])[CH2:27][O:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[C@H:21]3[S:20][CH:19]=[C:18]2[O:37][S:39]([CH3:38])(=[O:41])=[O:40])=[O:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 547082513-Hydroxy-7beta-phenoxyacetylamino-3-cephem-4-carboxylic acid diphenylmethyl ester

生成物 1

HCID 887625117beta-Phenoxyacetylamino-3-methanesulphonyloxy-2-cephem-4-carboxylic acid diphenylmethyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 50.6 g (98 mmols) of 7β-phenoxyacetylamino-3-hydroxy-3-cephem-4-carboxylic acid diphenylmethyl ester in 500 ml of methylene chloride is cooled to -20° C. and, after adding 14 ml of methanesulphonyl chloride (142 mmols), 22.3 ml (142 mmols) of triethylamine are added slowly. After a reaction period of 1 hour at -15° C. to -20° C. under nitrogen, the solution is washed with water, aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution. The organic phase is dried over sodium sulphate, concentrated in a rotary evaporator and dried under a high vacuum. A mixture consisting of 7β-phenoxyacetylamino-3-methanesulphonyloxy-3-cephem-4-carboxylic acid diphenylmethyl ester and 7β-phenoxyacetylamino-3-methanesulphonyloxy-2-cephem-4-carboxylic acid diphenylmethyl ester is obtained; thin layer chromatogram (silica gel; toluene/ethyl acetate, 2:1), 3-cephem derivative Rf=0.39; 2-cephem derivative Rf=0.32.

後処理

  1. additionare added slowly
  2. customAfter a reaction period of 1 hour at -15° C. to -20° C. under nitrogen
  3. washthe solution is washed with water, aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
  4. dry with materialThe organic phase is dried over sodium sulphate
  5. concentrationconcentrated in a rotary evaporator
  6. customdried under a high vacuum

出典と根拠

ORDレコード
ord-1a3411dd02564564ab832087b709235d
出典データセット
uspto-grants-1981_03
特許番号
US04256739

反応ノート

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