Acetone → 7-(2-thienylacetamido)-3-(1-methyl-1H-tetrazol-5-yl)vinyl-3-cephem-4-carboxylic acid

HRID 26040

反応式

HRID 26040 の反応式
[NH2:1][CH:2]1[C:20](=[O:21])[N:4]2[C:5]([C:17]([OH:19])=[O:18])=[C:6]([CH:9]=[CH:10][C:11]3[N:15]([CH3:16])[N:14]=[N:13][N:12]=3)[CH2:7][S:8][C@H:3]12.C(=O)([O-])O.[Na+].CC(C)=O.[S:31]1[CH:35]=[CH:34][CH:33]=[C:32]1[CH2:36][C:37](Cl)=[O:38]>O>[S:31]1[CH:35]=[CH:34][CH:33]=[C:32]1[CH2:36][C:37]([NH:1][CH:2]1[C:20](=[O:21])[N:4]2[C:5]([C:17]([OH:19])=[O:18])=[C:6]([CH:9]=[CH:10][C:11]3[N:15]([CH3:16])[N:14]=[N:13][N:12]=3)[CH2:7][S:8][C@H:3]12)=[O:38]

参加物

6

反応物 4

HCID 180Acetone2 回HCID 1623622-Thiopheneacetyl chlorideHCID 516892Sodium BicarbonateHCID 1317114727-amino-3-(1-methyl-1H-tetrazol-5-yl)vinyl-3-cephem-4-carboxylic acid

生成物 1

HCID 1317114717-(2-thienylacetamido)-3-(1-methyl-1H-tetrazol-5-yl)vinyl-3-cephem-4-carboxylic acid収率 101.1%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

In 40 ml of water were dissolved 416 mg of 7-amino-3-(1-methyl-1H-tetrazol-5-yl)vinyl-3-cephem-4-carboxylic acid and 660 mg of sodium hydrogencarbonate. To the solution was added 10 ml of acetone and further added dropwise with stirring at 0°-5° C., 20 ml of an acetone solution containing 323 mg of 2-thienylacetyl chloride. The mixture was stirred for 30 minutes under ice-cooling and for additional 3 hours at room temperature. The acetone was distilled off at room temperature under reduced pressure. The residual solution was washed with ether, adjusted to pH 2.0 with 10% hydrochloric acid and extracted with ethyl acetate. The extract was washed with an aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The ethyl acetate was removed under reduced pressure, and, upon washing the residue with ether, there was obtained 590 mg of 7-(2-thienylacetamido)-3-(1-methyl-1H-tetrazol-5-yl)vinyl-3-cephem-4-carboxylic acid.

後処理

  1. additionfurther added dropwise
  2. stirringThe mixture was stirred for 30 minutes under ice-
  3. distillationThe acetone was distilled off at room temperature under reduced pressure
  4. washThe residual solution was washed with ether
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with an aqueous sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe ethyl acetate was removed under reduced pressure
  9. washupon washing the residue with ether

出典と根拠

ORDレコード
ord-29b0d6884b9a4451b5e5cdca3673477c
出典データセット
uspto-grants-1979_04
特許番号
US04147863

関連ノート

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