Acetone → HCID 178511757, compound

HRID 619235Notes

Reaction equation

HRID 619235 reaction equation
[NH2:1][C@@H:2]1[C:33](=[O:34])[N:4]2[C:5]([C:17]([O:19]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:18])=[C:6]([S:9][CH2:10][S:11][C:12]3[N:13]=[N:14][NH:15][CH:16]=3)[CH2:7][S:8][C@H:3]12.Cl.CC(C)=O.C(OCC)(=O)C>C(O)=O>[NH2:1][C@@H:2]1[C:33](=[O:34])[N:4]2[C:5]([C:17]([OH:19])=[O:18])=[C:6]([S:9][CH2:10][S:11][C:12]3[N:13]=[N:14][NH:15][CH:16]=3)[CH2:7][S:8][C@H:3]12

Participants

6

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 178511754HCID 178511754, compound

Product 1

HCID 178511757HCID 178511757, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To a solution of diphenylmethyl 7β-amino-3-[(1H-1,2,3-triazol-4-yl)thiomethylthio]-3-cephem-4-carboxylate (9.9 g) in formic acid (39.6 ml) was added conc. hydrochloric acid (8.54 ml) at room temperature, and the mixture was stirred at the same temperature for 2.5 hours. The mixture was poured into a mixture of acetone (297 ml) and ethyl acetate (594 ml) under ice-cooling, and the resulting precipitate was collected by filtration. The precipitate was resolved in water, and adjusted to pH 4 with 28% ammonium hydroxide under ice-cooling. The precipitate was collected by filtration to give 7β-amino-3-[(1H-1,2,3-triazol-4-yl) thiomethylthio]-3-cephem-4-carboxylic acid (5.42 g).

Workup

  1. temperaturecooling
  2. filtrationthe resulting precipitate was collected by filtration
  3. temperaturecooling
  4. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-8b3182a776034a808ef4a9f659afbe31
Source dataset
uspto-grants-1999_09
Patent number
US05958914

Reaction notes

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