Hydrogen Bromide → 7-(2-Methoxyimino-3-oxo-4,4-dibromobutyramido)-3-cephem-4-carboxylic acid

HRID 1164263노트

반응식

HRID 1164263 반응식
C(OC(=O)C)(=O)C.C([O-])(=O)C.[Na+].C([O-])(=O)C.[K+].[CH3:18][O:19][N:20]=[C:21]([C:38](=[O:42])[CH:39]([Br:41])[Br:40])[C:22]([NH:24][CH:25]1[C:36](=[O:37])[N:27]2[CH:28]([C:33]([OH:35])=[O:34])[CH:29](O)[CH2:30][S:31][C@H:26]12)=[O:23].Br>O1CCCC1>[CH3:18][O:19][N:20]=[C:21]([C:38](=[O:42])[CH:39]([Br:40])[Br:41])[C:22]([NH:24][CH:25]1[C:36](=[O:37])[N:27]2[C:28]([C:33]([OH:35])=[O:34])=[CH:29][CH2:30][S:31][C@H:26]12)=[O:23]

참가 물질

7

반응물 5

HCID 260Hydrogen BromideHCID 7918Acetic AnhydrideHCID 517044Potassium AcetateHCID 517045Sodium AcetateHCID 867387467-(2-Methoxyimino-3-oxo-4,4-dibromobutyramido)-3-hydroxycepham-4-carboxylic acid

생성물 1

HCID 1317129327-(2-Methoxyimino-3-oxo-4,4-dibromobutyramido)-3-cephem-4-carboxylic acid수율 59.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Acetic anhydride (5 ml), sodium acetate (0.61 g) and potassium acetate (0.73 g) were added a solution of 7-(2-methoxyimino-3-oxo-4,4-dibromobutyramido)-3-hydroxycepham-4-carboxylic acid (syn isomer, 5 g) in dry tetrahydrofuran (50 ml), and stirred at 28° to 29° C. for 4 hours. After hydrogen bromide (5 ml) was added to the resultant solution, tetrahydrofuran was removed under reduced pressure therefrom. To the residue was added water (30 ml) and ethyl acetate (100 ml). The organic layer was separated, washed with water and 30% aqueous solution of sodium bromide in turn, and then dried over anhydrous magnesium sulfate. The solution was treated with activated charcoal, and concentrated under reduced pressure, and then the residue was pulverized with diisopropyl ether. The precipitates were collected by filtration, washed with diisopropyl ether and dried to give 7-(2-methoxyimino-3-oxo-4,4-dibromobutyramido)-3-cephem-4-carboxylic acid (syn isomer, 2.85 g).

후처리

  1. customwas removed under reduced pressure
  2. additionTo the residue was added water (30 ml) and ethyl acetate (100 ml)
  3. customThe organic layer was separated
  4. washwashed with water and 30% aqueous solution of sodium bromide in turn
  5. dry with materialdried over anhydrous magnesium sulfate
  6. additionThe solution was treated with activated charcoal
  7. concentrationconcentrated under reduced pressure
  8. filtrationThe precipitates were collected by filtration
  9. washwashed with diisopropyl ether
  10. customdried

출처 및 근거

ORD 기록
ord-7236957926244c41bef7965f1710ff64
출처 데이터셋
uspto-grants-1983_01
특허 번호
US04368325

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