Hydrochloric Acid → 2-Methyl-7-[2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid

HRID 28290Notes

Reaction equation

HRID 28290 reaction equation
C([O-])(=O)C.[Na+].[CH3:6][CH:7]1[CH:12]=[C:11]([C:13]([OH:15])=[O:14])[N:10]2[C:16](=[O:37])[CH:17]([NH:18][C:19](=[O:36])[C:20](=[N:33][O:34][CH3:35])[C:21]3[N:22]=[C:23]([NH:26]C(=O)C(F)(F)F)[S:24][CH:25]=3)[C@H:9]2[S:8]1.C(=O)(O)[O-].[Na+].Cl>O>[CH3:6][CH:7]1[CH:12]=[C:11]([C:13]([OH:15])=[O:14])[N:10]2[C:16](=[O:37])[CH:17]([NH:18][C:19](=[O:36])[C:20](=[N:33][O:34][CH3:35])[C:21]3[N:22]=[C:23]([NH2:26])[S:24][CH:25]=3)[C@H:9]2[S:8]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 1317114942-Methyl-7-[2-methoxyimino-2-(2-trifluoroacetylaminothiazol-4-yl)acetamido]-3-cephem-4-carboxylic acidHCID 178502767HCID 178502767, compound

Product 1

HCID 1317114962-Methyl-7-[2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of sodium acetate (11.6 g.) in water (43 ml) was added 2-methyl-7-[2-methoxyimino-2-(2-trifluoroacetylaminothiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid (syn isomer), which can be represented as 2-methyl-7-[2-methoxyimino-2-(2-trifluoroacetylimino-2,3-dihydrothiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid (syn isomer), (2.1 g.) with stirring, and the mixture was adjusted to pH 6 with 5% aqueous sodium bicarbonate solution. The mixture was stirred overnight at room temperature. After the reaction, the reaction mixture was adjusted to pH 2.8 to 3 with 10% hydrochloric acid and then cooled. The precipitates were collected by filtration and then dried to give 2-methyl-7-[2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid (syn isomer), which can be represented as 2-methyl-7-[2-methoxyimino-2-(2-imino-2,3-dihydrothiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid (syn isomer), (1.1 g.), dp>241° C. The same object compound (0.25 g.) was further obtained from the filtrate by a conventional manner.

Workup

  1. stirringThe mixture was stirred overnight at room temperature
  2. customAfter the reaction
  3. temperaturecooled
  4. filtrationThe precipitates were collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-5a26e0d64c1e41df857a2e426852b972
Source dataset
uspto-grants-1980_09
Patent number
US04225707

Reaction notes

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