Acetone → 7beta-Amino-3-[(pyrazol-4-yl)methylthio]-3-cephem-4-carboxylic acid

HRID 992692Notes

Reaction equation

HRID 992692 reaction equation
[NH2:1][C@@H:2]1[C:32](=[O:33])[N:4]2[C:5]([C:16]([O:18]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:17])=[C:6]([S:9][CH2:10][C:11]3[CH:12]=[N:13][NH:14][CH:15]=3)[CH2:7][S:8][C@H:3]12.Cl.C(OCC)(=O)C.CC(C)=O>C(O)=O>[NH2:1][C@@H:2]1[C:32](=[O:33])[N:4]2[C:5]([C:16]([OH:18])=[O:17])=[C:6]([S:9][CH2:10][C:11]3[CH:15]=[N:14][NH:13][CH:12]=3)[CH2:7][S:8][C@H:3]12

Participants

6

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 70122266Diphenylmethyl 7beta-amino-3-[(pyrazol-4-yl)methylthio]-3-cephem-4-carboxylate

Product 1

HCID 701245417beta-Amino-3-[(pyrazol-4-yl)methylthio]-3-cephem-4-carboxylic acidYield 68.1%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Diphenylmethyl 7β-amino-3-[(pyrazol-4-yl)methylthio]-3-cephem-4-carboxylate (810 mg) was dissolved in formic acid (3.2 ml) below 5° C. and herein concentrated hydrochloric acid (0.71 ml) was added thereto at the same temperature. After the reaction mixture was stirred at the room temperature for an hour, it was poured into a mixture of ethyl acetate (50 ml) and acetone (25 ml), resulting precipitate was collected by filtration, and dried under reduced pressure. The precipitate was suspended in a mixture of water (6.0 ml) and acetone (2.5 ml). After the suspension was dissolved at pH 7.0 with saturated sodium bicarbonate solution, and adjusted to pH 4.5 with 1N-hydrochloric acid. The mixture was stirred at the room temperature for 30 minutes, and then resulting precipitate was collected, washed with acetone (5.0 ml), and dried under reduced pressure to give 7β-amino-3-[(pyrazol-4-yl)methylthio]-3-cephem-4-carboxylic acid (0.36 g) was obtained.

Workup

  1. customresulting precipitate
  2. filtrationwas collected by filtration
  3. customdried under reduced pressure
  4. additionThe precipitate was suspended in a mixture of water (6.0 ml) and acetone (2.5 ml)
  5. dissolutionAfter the suspension was dissolved at pH 7.0 with saturated sodium bicarbonate solution
  6. stirringThe mixture was stirred at the room temperature for 30 minutes
  7. customresulting precipitate
  8. customwas collected
  9. washwashed with acetone (5.0 ml)
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-428c172c9bb348039702a97a76a9e606
Source dataset
uspto-grants-2002_10
Patent number
US06468995B1

Reaction notes

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