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Ethyl Acetate → 1-Propionyloxyethyl 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate

HRID 1463051
ノート
印刷プレビュー

反応式

HRID 1463051 の反応式
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:23][O:24][CH3:25])[C:8]([NH:10][CH:11]2[C:21](=[O:22])[N:13]3[C:14]([C:18]([OH:20])=[O:19])=[CH:15][CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.C(=O)([O-])[O-].[K+].[K+].[C:32]([O:36][CH:37](Cl)[CH3:38])(=[O:35])[CH2:33][CH3:34].C(OCC)(=O)C>CS(C)=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:23][O:24][CH3:25])[C:8]([NH:10][CH:11]2[C:21](=[O:22])[N:13]3[C:14]([C:18]([O:20][CH:37]([O:36][C:32](=[O:35])[CH2:33][CH3:34])[CH3:38])=[O:19])=[CH:15][CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 135066761-Chloroethyl propionateHCID 1317124447-[2-(2-Amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid

生成物 1

HCID 1317136041-Propionyloxyethyl 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate収率 63.4%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

To a solution of 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid (syn-isomer, 100 g) in dimethylsulfoxide (650 ml) was added potassium carbonate (21.6 g). Thereto was added 1-chloroethyl propionate (42.8 g) at 40° C. and the mixture was stirred at the same temperature for 2 hours. The reaction mixture was poured into a mixture of ice-water (3 l) and ethyl acetate (2 l), and the separated organic layer was washed in turn with 5% aqueous sodium bicarbonate (300 ml×2), water (300 ml) and an aqueous sodium chloride, followed by drying over magnesium sulfate. After treating with activated charcoal, the solvent was removed by evaporation, and the residue was pulverized with diisopropyl ether to give 1-propionyloxyethyl 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (syn-isomer, 80 g).

後処理

  1. washthe separated organic layer was washed in turn with 5% aqueous sodium bicarbonate (300 ml×2), water (300 ml)
  2. dry with materialby drying over magnesium sulfate
  3. additionAfter treating with activated charcoal
  4. customthe solvent was removed by evaporation

出典と根拠

ORDレコード
ord-aa1dd4350953410aac9900992e5093d3
出典データセット
uspto-grants-1984_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04463002

反応ノート

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