Hydrochloric Acid → 7-[2-Isopropoxyimino-2-(2-amino-1,3-thiazol-4-yl)acetamido]-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid

HRID 1388482Notes

Reaction equation

HRID 1388482 reaction equation
Cl.[CH:2]([O:5][N:6]=[C:7]([C:28]1[N:29]=[C:30]([NH:33]C=O)[S:31][CH:32]=1)[C:8]([NH:10][CH:11]1[C:26](=[O:27])[N:13]2[C:14]([C:23]([OH:25])=[O:24])=[C:15]([CH2:18][O:19][C:20](=[O:22])[NH2:21])[CH2:16][S:17][C@H:12]12)=[O:9])([CH3:4])[CH3:3]>O1CCCC1.CO>[CH:2]([O:5][N:6]=[C:7]([C:28]1[N:29]=[C:30]([NH2:33])[S:31][CH:32]=1)[C:8]([NH:10][CH:11]1[C:26](=[O:27])[N:13]2[C:14]([C:23]([OH:25])=[O:24])=[C:15]([CH2:18][O:19][C:20](=[O:22])[NH2:21])[CH2:16][S:17][C@H:12]12)=[O:9])([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 1317127307-[2-Isopropoxyimino-2-(2-formamido-1,3-thiazol-4-yl)acetamido]-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid

Product 1

HCID 1317127357-[2-Isopropoxyimino-2-(2-amino-1,3-thiazol-4-yl)acetamido]-3-carbamoyloxymethyl-3-cephem-4-carboxylic acidYield 20.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Conc. hydrochloric acid (1 ml) was added to a solution of 7-[2-isopropoxyimino-2-(2-formamido-1,3-thiazol-4-yl)acetamido]-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid (syn isomer)(1.3 g) in a mixture of tetrahydrofuran (10 ml) and methanol (10 ml). The mixture was stirred for 3.5 hours at ambient temperature and then concentrated to dryness. Water was added to the residue and to the mixture was added sodium bicarbonate to give a solution. The solution was adjusted to pH 3.0 with conc. hydrochloric acid under ice-cooling. Precipitates were collected by filtration, washed with water and dried to give 7-[2-isopropoxyimino-2-(2-amino-1,3-thiazol-4-yl)acetamido]-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid (syn isomer)(0.25 g).

Workup

  1. concentrationconcentrated to dryness
  2. additionWater was added to the residue and to the mixture
  3. additionwas added sodium bicarbonate
  4. customto give a solution
  5. temperaturecooling
  6. customPrecipitates
  7. filtrationwere collected by filtration
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-13da5b96adb54feab0707b78f103a619
Source dataset
uspto-grants-1984_02
Patent number
US04431643

Reaction notes

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