Hydrochloric Acid → 3-Hydroxy-7beta-phenoxyacetylamino-cepham-4alpha-carboxylic acid diphenylmethyl ester

HRID 1155336ノート

反応式

HRID 1155336 の反応式
[BH4-].[Na+].[C:3]1([CH:9]([O:16][C:17]([C:19]2[N:24]3[C:25](=[O:38])[C@@H:26]([NH:27][C:28](=[O:37])[CH2:29][O:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C@H:23]3[S:22][CH2:21][C:20]=2[OH:39])=[O:18])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl>CN(C)C=O.C(O)=O>[C:3]1([CH:9]([O:16][C:17]([C@@H:19]2[N:24]3[C:25](=[O:38])[C@@H:26]([NH:27][C:28](=[O:37])[CH2:29][O:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C@H:23]3[S:22][CH2:21][CH:20]2[OH:39])=[O:18])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 547082513-Hydroxy-7beta-phenoxyacetylamino-3-cephem-4-carboxylic acid diphenylmethyl ester

生成物 1

HCID 705700963-Hydroxy-7beta-phenoxyacetylamino-cepham-4alpha-carboxylic acid diphenylmethyl ester収率 77.8%

試薬・触媒・溶媒 2

HCID 284Formic Acid溶媒HCID 6228Dimethylformamide溶媒

実験手順

28.4 mg of sodium borohydride are added to a solution of 516 mg of 3-hydroxy-7β-phenoxyacetylamino-3-cephem-4-carboxylic acid diphenylmethyl ester in 4 ml of dimethylformamide and 1 ml of formic acid at room temperature. After stirring the reaction mixture for one hour at room temperature, it is poured onto a mixture of ice and 2 N hydrochloric acid and extracted with ethyl acetate. The combined organic phases are washed successively with water, three times with saturated sodium bicarbonate solution and saturated, aqueous sodium chloride solution, dried over sodium sulphate and concentrated in vacuo. The residue is substantially freed from dimethylformamide under a high vacuum. The resulting white foam (580 mg) is subjected to chromatography on preparative silica gel thick-layer plates with toluene/ethyl acetate 1:1 and yields 403 mg of the title compound.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe combined organic phases are washed successively with water, three times with saturated sodium bicarbonate solution
  3. dry with materialsaturated, aqueous sodium chloride solution, dried over sodium sulphate
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-ec64a0c6c9e049e8954f9e5c058ca374
出典データセット
uspto-grants-1981_11
特許番号
US04301279

反応ノート

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