Hydrochloric Acid → HCID 131712739, compound

HRID 1388484Notes

Reaction equation

HRID 1388484 reaction equation
Cl.[CH:2]([O:5][N:6]=[C:7]([C:31]1[N:32]=[C:33]([NH:36]C=O)[S:34][CH:35]=1)[C:8]([NH:10][CH:11]1[C:29](=[O:30])[N:13]2[C:14]([C:26]([OH:28])=[O:27])=[C:15]([CH2:18][S:19][C:20]3[N:24]([CH3:25])[N:23]=[N:22][N:21]=3)[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:31]1[N:32]=[C:33]([NH2:36])[S:34][CH:35]=1)[C:8]([NH:10][CH:11]1[C:29](=[O:30])[N:13]2[C:14]([C:26]([OH:28])=[O:27])=[C:15]([CH2:18][S:19][C:20]3[N:24]([CH3:25])[N:23]=[N:22][N:21]=3)[CH2:16][S:17][C@H:12]12)=[O:9])([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 131712734HCID 131712734, compound

Product 1

HCID 131712739HCID 131712739, compoundYield 56.1%

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-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer)(1.5 g) in a mixture of tetrahydrofuran (12 ml) and methanol (12 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-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer)(0.8 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-0dadd4d7ff5a423eab4f346b100e287c
Source dataset
uspto-grants-1984_02
Patent number
US04431643

Reaction notes

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