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

HRID 26040

반응식

HRID 26040 반응식
[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]

참가 물질

6

반응물 4

HCID 180Acetone2회HCID 1623622-Thiopheneacetyl chlorideHCID 516892Sodium BicarbonateHCID 1317114727-amino-3-(1-methyl-1H-tetrazol-5-yl)vinyl-3-cephem-4-carboxylic acid

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-29b0d6884b9a4451b5e5cdca3673477c
출처 데이터셋
uspto-grants-1979_04
특허 번호
US04147863

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