Water → Benzhydryl 7-(4-bromo-3,3-diethoxy-2-methoxyiminobutyramido)-3-vinyl-3-cephem-4-carboxylate

HRID 1381385Notes

Reaction equation

HRID 1381385 reaction equation
Cl.[NH2:2][CH:3]1[C:28](=[O:29])[N:5]2[C:6]([C:12]([O:14][CH:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])=[C:7]([CH:10]=[CH2:11])[CH2:8][S:9][C@H:4]12.C[Si](CC(N)=O)(C)C.[Br:38][CH2:39][C:40]([O:51][CH2:52][CH3:53])([O:48][CH2:49][CH3:50])[C:41](=[N:45][O:46][CH3:47])[C:42](Cl)=[O:43].O>C(OCC)(=O)C>[Br:38][CH2:39][C:40]([O:51][CH2:52][CH3:53])([O:48][CH2:49][CH3:50])[C:41](=[N:45][O:46][CH3:47])[C:42]([NH:2][CH:3]1[C:28](=[O:29])[N:5]2[C:6]([C:12]([O:14][CH:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[O:13])=[C:7]([CH:10]=[CH2:11])[CH2:8][S:9][C@H:4]12)=[O:43]

Participants

6

Reactant 4

HCID 962WaterHCID 357676Acetamide, 2-(trimethylsilyl)-HCID 12818005Benzhydryl 7-amino-3vinyl-3cephem-4-carboxylate hydrochlorideHCID 542161602-Methoxyimino-3,3-diethoxy-4-bromobutyryl chloride

Product 1

HCID 131713161Benzhydryl 7-(4-bromo-3,3-diethoxy-2-methoxyiminobutyramido)-3-vinyl-3-cephem-4-carboxylateYield 100.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of benzhydryl 7-amino-3-vinyl-3-cephem-4-carboxylate hydrochloride (6.4 g) and trimethylsilylacetamide (9.8 g) in ethyl acetate (80 ml) was added 4-bromo-3,3-diethoxy-2-methoxyiminobutyryl chloride (syn isomer) (5.0 g) at -20° C. with stirring, and the stirring was continued at -20° to -5° C. for an hour. To the reaction mixture were added ethyl acetate and water, and the separated ethyl acetate solution was washed with a saturated aqueous sodium bicarbonate and an aqueous sodium chloride, followed by drying over anhydrous magnesium sulfate. Removal of the solvent gave benzhydryl 7-(4-bromo-3,3-diethoxy-2-methoxyiminobutyramido)-3-vinyl-3-cephem-4-carboxylate (syn isomer) (10.1 g).

Workup

  1. waitthe stirring was continued at -20° to -5° C. for an hour
  2. washthe separated ethyl acetate solution was washed with a saturated aqueous sodium bicarbonate
  3. dry with materialby drying over anhydrous magnesium sulfate
  4. customRemoval of the solvent

Sources & evidence

ORD record
ord-859559a697ab44d7b7708953f678f14c
Source dataset
uspto-grants-1986_04
Patent number
US04585860

Reaction notes

Loading…