Hydrochloric Acid → 7-[2-(2-Aminothiazol-4-yl)-2-methoxycarbonylmethoxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylic acid

HRID 1656259Notes

Reaction equation

HRID 1656259 reaction equation
Cl[CH2:2][C:3](=O)[C:4](=[N:22][O:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])[C:5]([NH:7][CH:8]1[C:20](=[O:21])[N:10]2[C:11]([C:17]([OH:19])=[O:18])=[C:12]([CH:15]=[CH2:16])[CH2:13][S:14][C@H:9]12)=[O:6].[NH2:30][C:31]([NH2:33])=[S:32].C([O-])(=O)C.[Na+].Cl>O>[NH2:33][C:31]1[S:32][CH:2]=[C:3]([C:4](=[N:22][O:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])[C:5]([NH:7][CH:8]2[C:20](=[O:21])[N:10]3[C:11]([C:17]([OH:19])=[O:18])=[C:12]([CH:15]=[CH2:16])[CH2:13][S:14][C@H:9]23)=[O:6])[N:30]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 517045Sodium AcetateHCID 2723790ThioureaHCID 1317140607-(4-Chloro-2-methoxycarbonylmethoxyimino-3-oxobutyramido)-3-vinyl-3-cephem-4-carboxylic acid

Product 1

HCID 911897697-[2-(2-Aminothiazol-4-yl)-2-methoxycarbonylmethoxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylic acidYield 90.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 7-(4-chloro-2-methoxycarbonylmethoxyimino-3-oxobutyramido)-3-vinyl-3-cephem-4-carboxylic acid (syn isomer) (2.0 g) in water (20 ml) were added thiourea (0.683 g) and sodium acetate (1.84 g) at 40° C. with stirring. The reaction mixture was stirred at the same temperature for 1.5 hours. The resultant solution was adjusted to pH 2.8 with 10% hydrochloric acid and stirred under ice-cooling for 20 minutes. The precipitates were collected by filtration, washed with water and dried over phosphorus pentoxide under reduced pressure to give 7-[2-(2-aminothiazol-4-yl)-2-methoxycarbonylmethoxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylic acid (syn isomer) (1.9 g).

Workup

  1. stirringThe reaction mixture was stirred at the same temperature for 1.5 hours
  2. stirringstirred under ice-
  3. temperaturecooling for 20 minutes
  4. filtrationThe precipitates were collected by filtration
  5. washwashed with water
  6. dry with materialdried over phosphorus pentoxide under reduced pressure

Sources & evidence

ORD record
ord-f9ea9a70c4554d9e8d6a516f7312c9ff
Source dataset
uspto-grants-1993_10
Patent number
US05252731

Reaction notes

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