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

HRID 2412753Notes

Reaction equation

HRID 2412753 reaction equation
Cl.[CH2:2]([O:5][N:6]=[C:7]([C:33]1[N:34]=[C:35]([NH:38]C=O)[S:36][CH:37]=1)[C:8]([NH:10][CH:11]1[C:31](=[O:32])[N:13]2[C:14]([C:28]([OH:30])=[O:29])=[C:15]([CH2:18][S:19][C:20]3[N:24]([CH2:25][CH:26]=[CH2:27])[N:23]=[N:22][N:21]=3)[CH2:16][S:17][C@H:12]12)=[O:9])[CH:3]=[CH2:4]>CO>[CH2:2]([O:5][N:6]=[C:7]([C:33]1[N:34]=[C:35]([NH2:38])[S:36][CH:37]=1)[C:8]([NH:10][CH:11]1[C:31](=[O:32])[N:13]2[C:14]([C:28]([OH:30])=[O:29])=[C:15]([CH2:18][S:19][C:20]3[N:24]([CH2:25][CH:26]=[CH2:27])[N:23]=[N:22][N:21]=3)[CH2:16][S:17][C@H:12]12)=[O:9])[CH:3]=[CH2:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 1317125787-[2-allyloxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(1-allyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid

Product 1

HCID 1317125867-[2-allyloxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-(1-allyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acidYield 76.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Conc. hydrochloric acid (0.33 g) was added to a solution of 7-[2-allyloxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(1-allyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer)(1.30 g) in methanol (13 ml) and the mixture was stirred for 4.5 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 (25 ml). The aqueous solution was washed with ethyl acetate (25 ml) and adjusted to pH 2.0 with 10% hydrochloric acid. Precipitates were collected by filtration, washed with water and dried to give colorless powder of 7-[2-allyloxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-(1-allyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer)(0.95 g).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. dissolutionthe residue was dissolved in a saturated aqueous solution of sodium bicarbonate (25 ml)
  3. washThe aqueous solution was washed with ethyl acetate (25 ml)
  4. customPrecipitates
  5. filtrationwere collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-85371b40f1e44f3cbaf87407a4024667
Source dataset
uspto-grants-1985_01
Patent number
US04493833

Reaction notes

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