Acetone → 7-[2-Ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate acetone

HRID 647242Notes

Reaction equation

HRID 647242 reaction equation
[CH2:1]([O:3][N:4]=[C:5]([C:28]1[N:32]=[C:31]([NH2:33])[S:30][N:29]=1)[C:6]([NH:8][CH:9]1[C:26](=[O:27])[N:11]2[C:12]([C:23]([O-:25])=[O:24])=[C:13]([CH2:16][N+:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:14][S:15][C@H:10]12)=[O:7])[CH3:2].[CH3:34][C:35]([CH3:37])=[O:36]>O>[CH3:34][C:35]([CH3:37])=[O:36].[CH2:1]([O:3][N:4]=[C:5]([C:28]1[N:32]=[C:31]([NH2:33])[S:30][N:29]=1)[C:6]([NH:8][CH:9]1[C:26](=[O:27])[N:11]2[C:12]([C:23]([O-:25])=[O:24])=[C:13]([CH2:16][N+:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:14][S:15][C@H:10]12)=[O:7])[CH3:2]

Participants

4

Reactant 2

HCID 180AcetoneHCID 1317127507-[2-Ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate

Product 1

HCID 1317127487-[2-Ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate acetone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A powder (0.2 g) of 7-[2-ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate (syn isomer) was dissolved in water (0.8 ml) and dropped acetone (1.6 ml) thereto under stirring at ambient temperature. After few minutes, the stirring was stopped and the solution was stood for 1.5 hours at ambient temperature to crystallize. The resulting colorless needles were filtered, washed with 90% aqueous acetone (1 ml×2) and acetone (1 ml×3) and dried for 9 hours under reduced pressure to give colorless needles of 7-[2-ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate acetone adduct monohydrate (syn isomer)(120 mg), mp>155° C. (dec.).

Workup

  1. waitAfter few minutes
  2. customto crystallize
  3. filtrationThe resulting colorless needles were filtered
  4. washwashed with 90% aqueous acetone (1 ml×2) and acetone (1 ml×3)
  5. customdried for 9 hours under reduced pressure

Sources & evidence

ORD record
ord-cdddd2dd0428471ea5564e07e4d78449
Source dataset
uspto-grants-1983_10
Patent number
US04408042

Reaction notes

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