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

HRID 1463043노트

반응식

HRID 1463043 반응식
[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])=[O:19])=[CH:15][CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[Na+].[C:27]([O:31][CH:32](Br)[CH3:33])(=[O:30])[CH2:28][CH3:29].[I-].[Na+].O>CS(C)=O.C(OCC)(=O)C>[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:32]([O:31][C:27](=[O:30])[CH2:28][CH3:29])[CH3:33])=[O:19])=[CH:15][CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 5238Sodium IodideHCID 132328531-Bromoethyl propionateHCID 131712445Sodium 7-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate

생성물 1

HCID 1317136041-Propionyloxyethyl 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate수율 17.4%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of sodium 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (syn-isomer, 4.0 g) in dimethylsulfoxide (40 ml) were added 1-bromoethyl propionate (1.8 g) and sodium iodide (0.18 g), and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was poured into a mixture of cold water and ethyl acetate, and the organic layer was separated. The remaining aqueous layer was extracted with ethyl acetate. The extract and the organic layer were combined, washed with water and dried over magnesium sulfate. The solvent was then distilled off and the residue was subjected to column chromatography using silica gel (50 g), elution being carried out with a mixture of benzene and ethyl acetate (3:2, v/v). The fractions containing the desired product were combined and the solvent was distilled off to give 1-propionyloxyethyl 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer, 0.83 g), mp 113°-116° C. (decompn.).

후처리

  1. customthe organic layer was separated
  2. extractionThe remaining aqueous layer was extracted with ethyl acetate
  3. extractionThe extract
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was then distilled off
  7. washsilica gel (50 g), elution
  8. additionbeing carried out with a mixture of benzene and ethyl acetate (3:2
  9. additionThe fractions containing the desired product
  10. distillationthe solvent was distilled off

출처 및 근거

ORD 기록
ord-e8b3e2a5f489449bbc3ac8c1ecb95489
출처 데이터셋
uspto-grants-1984_07
특허 번호
US04463002

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