Hydrochloric Acid → HCID 131712603, compound

HRID 2412795Notes

Reaction equation

HRID 2412795 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:28]1[N:29]=[C:30]([NH:33]C=O)[S:31][CH:32]=1)[C:5]([NH:7][CH:8]1[C:26](=[O:27])[N:10]2[C:11]([C:23]([OH:25])=[O:24])=[C:12]([CH2:15][S:16][C:17]3[S:21][N:20]=[C:19]([CH3:22])[N:18]=3)[CH2:13][S:14][C@H:9]12)=[O:6].Cl>CO>[CH3:1][O:2][N:3]=[C:4]([C:28]1[N:29]=[C:30]([NH2:33])[S:31][CH:32]=1)[C:5]([NH:7][CH:8]1[C:26](=[O:27])[N:10]2[C:11]([C:23]([OH:25])=[O:24])=[C:12]([CH2:15][S:16][C:17]3[S:21][N:20]=[C:19]([CH3:22])[N:18]=3)[CH2:13][S:14][C@H:9]12)=[O:6]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131712604HCID 131712604, compound

Product 1

HCID 131712603HCID 131712603, compoundYield 64.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 7-[2-methoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(3-methyl-1,2,4-thiadiazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (2.2 g.), conc. hydrochloric acid (0.8 ml.) and methanol (16 ml.) was stirred for 3 hours at ambient temperature. The solvent was distilled off under reduced pressure and the residue was dissolved in a saturated aqueous solution of sodium bicarbonate (pH 7.5). The aqueous solution was adjusted to pH 3.5 with 10% hydrochloric acid and stirred for 1 hour. Precipitates were collected by filtration, washed with water and dried to give 7-[2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-(3-methyl-1,2,4-thiadiazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (1.35 g.).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. dissolutionthe residue was dissolved in a saturated aqueous solution of sodium bicarbonate (pH 7.5)
  3. stirringstirred for 1 hour
  4. customPrecipitates
  5. filtrationwere collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-a14d277c5745485080a33c20e6fcc6f9
Source dataset
uspto-grants-1985_01
Patent number
US04493833

Reaction notes

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