Hydrochloric Acid → Diphenylmethyl 7beta-amino-3-[(pyrazol-4-yl)methylthio]-3-cephem-4-carboxylate

HRID 992690Notes

Reaction equation

HRID 992690 reaction equation
C([NH:3][C@@H:4]1[C:34](=[O:35])[N:6]2[C:7]([C:18]([O:20][CH:21]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])=[C:8]([S:11][CH2:12][C:13]3[CH:14]=[N:15][NH:16][CH:17]=3)[CH2:9][S:10][C@H:5]12)=O.Cl>CO>[NH2:3][C@@H:4]1[C:34](=[O:35])[N:6]2[C:7]([C:18]([O:20][CH:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:19])=[C:8]([S:11][CH2:12][C:13]3[CH:17]=[N:16][NH:15][CH:14]=3)[CH2:9][S:10][C@H:5]12

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 88158715Diphenylmethyl 7beta-formamido-3-[(pyrazol-4-yl)methylthio]-3-cephem-4-carboxylate

Product 1

HCID 70122266Diphenylmethyl 7beta-amino-3-[(pyrazol-4-yl)methylthio]-3-cephem-4-carboxylateYield 53.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Diphenylmethyl 7β-formamido-3-[(pyrazol-4-yl)methylthio]-3-cephem-4-carboxylate (2.96 g) was dissolved in methanol (30 ml) and concentrated hydrochloric acid (2.2 ml) was added thereto at the room temperature. Stirring was continued for 3 hours, then solvent was evaporated. The residue was diluted with a mixture of water. The ethyl acetate and aqueous layer was adjusted to pH 6.5 with 30% aqueous potassium carbonate. The organic layer was separated, washed with water and brine, and dried over magnesium sulfate. Solvent was evaporated to afford diphenylmethyl 7β-amino-3-[(pyrazol-4-yl)methylthio]-3-cephem-4-carboxylate (1.50 g).

Workup

  1. customat the room temperature
  2. customsolvent was evaporated
  3. additionThe residue was diluted with a mixture of water
  4. customThe organic layer was separated
  5. washwashed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customSolvent was evaporated

Sources & evidence

ORD record
ord-232287c678014d689d62c84b43b2b9da
Source dataset
uspto-grants-2002_10
Patent number
US06468995B1

Reaction notes

Loading…