Hydrochloric Acid → 7-[2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-(1-hexyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid

HRID 2412796Notes

Reaction equation

HRID 2412796 reaction equation
Cl.[CH3:2][O:3][N:4]=[C:5]([C:34]1[N:35]=[C:36]([NH:39]C=O)[S:37][CH:38]=1)[C:6]([NH:8][CH:9]1[C:32](=[O:33])[N:11]2[C:12]([C:29]([OH:31])=[O:30])=[C:13]([CH2:16][S:17][C:18]3[N:22]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[N:21]=[N:20][N:19]=3)[CH2:14][S:15][C@H:10]12)=[O:7]>CO>[CH3:2][O:3][N:4]=[C:5]([C:34]1[N:35]=[C:36]([NH2:39])[S:37][CH:38]=1)[C:6]([NH:8][CH:9]1[C:32](=[O:33])[N:11]2[C:12]([C:29]([OH:31])=[O:30])=[C:13]([CH2:16][S:17][C:18]3[N:22]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[N:21]=[N:20][N:19]=3)[CH2:14][S:15][C@H:10]12)=[O:7]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 1317126017-[2-methoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(1-hexyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid

Product 1

HCID 1317126057-[2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-(1-hexyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acidYield 80.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Conc. hydrochloric acid (2.1 g.) was added under ice-cooling and stirring to a solution of 7-[2-methoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(1-hexyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (6.0 g.) in methanol (60 ml.), and the mixture was stirred for 4 hours at ambient temperature. The solvent was removed from the reaction mixture and ethyl acetate (50 g.) was added thereto. The mixture was adjusted to pH 7.0 under stirring with a saturated aqueous solution of sodium bicarbonate. The aqueous layer was separated, washed with ethyl acetate and adjusted to pH 3.5 with conc. hydrochloric acid. Precipitates were collected by filtration, washed with water and dried under reduced pressure to give powder of 7-[2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-(1-hexyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (4.62 g.).

Workup

  1. temperaturecooling
  2. customThe solvent was removed from the reaction mixture and ethyl acetate (50 g.)
  3. additionwas added
  4. stirringunder stirring with a saturated aqueous solution of sodium bicarbonate
  5. customThe aqueous layer was separated
  6. washwashed with ethyl acetate
  7. customPrecipitates
  8. filtrationwere collected by filtration
  9. washwashed with water
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-4189c3268ba04030bb38138ad4ed4d61
Source dataset
uspto-grants-1985_01
Patent number
US04493833

Reaction notes

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