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

HRID 904877Notes

Reaction equation

HRID 904877 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:35]1[N:36]=[C:37]([NH:40]C(=O)C(F)(F)F)[S:38][CH:39]=1)[C:5]([NH:7][CH:8]1[C:33](=[O:34])[N:10]2[C:11]([C:30]([OH:32])=[O:31])=[C:12]([CH2:15][S:16][C:17]3[N:21]([CH2:22][C:23]([C:27]([OH:29])=[O:28])=[N:24][O:25][CH3:26])[N:20]=[N:19][N:18]=3)[CH2:13][S:14][C@H:9]12)=[O:6].O.O.O.C([O-])(=O)C.[Na+].Cl>O>[CH3:1][O:2][N:3]=[C:4]([C:35]1[N:36]=[C:37]([NH2:40])[S:38][CH:39]=1)[C:5]([NH:7][CH:8]1[C:33](=[O:34])[N:10]2[C:11]([C:30]([OH:32])=[O:31])=[C:12]([CH2:15][S:16][C:17]3[N:21]([CH2:22][C:23]([C:27]([OH:29])=[O:28])=[N:24][O:25][CH3:26])[N:20]=[N:19][N:18]=3)[CH2:13][S:14][C@H:9]12)=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23665404Sodium Acetate TrihydrateHCID 1317132447-[2-methoxyimino-2-{2-(2,2,2-trifluoroacetamido)thiazol-4-yl}acetamido]-3-[1-(2-carboxy-2-methoxyiminoethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid

Product 1

HCID 1317132487-[2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-[1-(2-carboxy-2-methoxyiminoethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 7-[2-methoxyimino-2-{2-(2,2,2-trifluoroacetamido)thiazol-4-yl}acetamido]-3-[1-(2-carboxy-2-methoxyiminoethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid (syn isomer: in the 7-position) (1.70 g) and sodium acetate. trihydrate (3.26 g) in water (14 ml) was stirred overnight at room temperature. The solution was adjusted to pH 2.5 with 10% hydrochloric acid under ice-cooling and the resultant precipitates were filtered and washed with water to give 7-[2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-[1-(2-carboxy-2-methoxyiminoethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid (syn isomer: in the 7-position).

Workup

  1. temperaturecooling
  2. customthe resultant precipitates
  3. filtrationwere filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-4ef5d1ebd5ad49f7a077a6788d072cbd
Source dataset
uspto-grants-1983_12
Patent number
US04420477

Reaction notes

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