Water → 7beta-[2-(2-Amino-5-chloro-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid phthalidyl ester

HRID 126905

反応式

HRID 126905 の反応式
[NH2:1][C:2]1[S:3][C:4]([Cl:26])=[C:5]([C:7](=[N:23][O:24][CH3:25])[C:8]([NH:10][C@@H: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(N(CC)CC)C.[C:34]1([C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37](Br)[O:36]1)=[O:35].O>CN(C)C=O>[C:34]1([C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37]([O:19][C:18]([C:14]2[N:13]3[C:21](=[O:22])[C@@H:11]([NH:10][C:8](=[O:9])[C:7]([C:5]4[N:6]=[C:2]([NH2:1])[S:3][C:4]=4[Cl:26])=[N:23][O:24][CH3:25])[C@H:12]3[S:17][CH2:16][CH:15]=2)=[O:20])[O:36]1)=[O:35]

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 962181(3H)-Isobenzofuranone, 3-bromo-HCID 1317121027beta-[2-(2-Amino-5-chloro-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid

生成物 1

HCID 1317121087beta-[2-(2-Amino-5-chloro-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid phthalidyl ester収率 80%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 7β-[2-(2-amino-5-chloro-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid (209 mg) in N,N-dimethylformamide (5 ml) are added triethylamine (0.07 ml) and phthalidyl bromide (128 mg), and the mixture is stirred at room temperature for 20 minutes. The reaction mixture is poured into water and the separated precipitate is collected by filtration. The solid material is dissolved in ethyl acetate, washed with water, diluted aqueous sodium hydrogen carbonate solution, water, diluted aqueous phosphoric acid and water, dried, and evaporated. Purification of the residue by silica gel column chromatography gives 7β-[2-(2-amino-5-chloro-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid phthalidyl ester (220 mg).

後処理

  1. filtrationthe separated precipitate is collected by filtration
  2. dissolutionThe solid material is dissolved in ethyl acetate
  3. washwashed with water, diluted aqueous sodium hydrogen carbonate solution, water, diluted aqueous phosphoric acid and water
  4. customdried
  5. customevaporated
  6. customPurification of the residue by silica gel column chromatography

出典と根拠

ORDレコード
ord-4e3ef60a8e184445b7789b10ae164850
出典データセット
uspto-grants-1981_03
特許番号
US04254119

関連ノート

読み込み中…