Diethyl Ether → Benzhydryl 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylate

HRID 1195557Notes

Reaction equation

HRID 1195557 reaction equation
Br[CH2:2][C:3](=O)[C:4](=[N:35][O:36][CH3:37])[C:5]([NH:7][CH:8]1[C:33](=[O:34])[N:10]2[C:11]([C:17]([O:19][CH:20]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])=[C:12]([CH:15]=[CH2:16])[CH2:13][S:14][C@H:9]12)=[O:6].[NH2:39][C:40]([NH2:42])=[S:41].C([O-])(=O)C.[Na+].C(OCC)C>O.O1CCCC1>[NH2:42][C:40]1[S:41][CH:2]=[C:3]([C:4](=[N:35][O:36][CH3:37])[C:5]([NH:7][CH:8]2[C:33](=[O:34])[N:10]3[C:11]([C:17]([O:19][CH:20]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[O:18])=[C:12]([CH:15]=[CH2:16])[CH2:13][S:14][C@H:9]23)=[O:6])[N:39]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 517045Sodium AcetateHCID 2723790ThioureaHCID 131713160Benzhydryl 7-(4-bromo-2-methoxyiminoacetoacetamido)-3-vinyl-3-cephem-4-carboxylate

Product 1

HCID 131713191Benzhydryl 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylateYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of benzhydryl 7-(4-bromo-2-methoxyiminoacetoacetamido)-3-vinyl-3-cephem-4-carboxylate (syn isomer) (1.2 g), thiourea (0.5 g) and sodium acetate (trihydrate) (0.7 g) in water (20 ml) and tetrahydrofuran (20 ml) was stirred at 30° C. for 3.5 hours. The reaction mixture was extracted with ethyl acetate, and the extract was washed with water and dried over anhydrous magnesium sulfate. Removal of the solvent gave a residue, which was pulverized with diethyl ether to obtain benzhydryl 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylate (syn isomer) (1.05 g).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washthe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customRemoval of the solvent
  5. customgave a residue, which

Sources & evidence

ORD record
ord-bae90cac7407423494ba22ed5e52265f
Source dataset
uspto-grants-1992_05
Patent number
US05110921

Reaction notes

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