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

HRID 1155660Notes

Reaction equation

HRID 1155660 reaction equation
CC(C)=O.[CH2:5]([O:7][N:8]=[C:9]([C:32]1[N:36]=[C:35]([NH2:37])[S:34][N:33]=1)[C:10]([NH:12][CH:13]1[C:30](=[O:31])[N:15]2[C:16]([C:27]([O-:29])=[O:28])=[C:17]([CH2:20][N+:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:18][S:19][C@H:14]12)=[O:11])[CH3:6]>O>[CH2:5]([O:7][N:8]=[C:9]([C:32]1[N:36]=[C:35]([NH2:37])[S:34][N:33]=1)[C:10]([NH:12][CH:13]1[C:30](=[O:31])[N:15]2[C:16]([C:27]([O-:29])=[O:28])=[C:17]([CH2:20][N+:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:18][S:19][C@H:14]12)=[O:11])[CH3:6]

Participants

3

Reactant 1

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

Product 1

HCID 1317127507-[2-Ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylateYield 58.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 7-[2-ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate acetone adduct (syn isomer) (1.0 g) in water (1 ml) was stood on for 5 days in a freezer at -20° C. A mixture of ice and precipitates was stood on at ambient temperature until the ice was melted. The resulting precipitates were collected by filtration, washed with water (0.3 ml) and dried in vacuo to give 7-[2-ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate (syn isomer) (0.52 g) as colorless needles, mp 165° to 170° C. (dec.).

Workup

  1. customwas stood on for 5 days in a freezer at -20° C
  2. additionA mixture of ice
  3. customprecipitates
  4. customwas stood on at ambient temperature until the ice
  5. customThe resulting precipitates
  6. filtrationwere collected by filtration
  7. washwashed with water (0.3 ml)
  8. customdried in vacuo

Sources & evidence

ORD record
ord-350a1cd3ac064dc2abae0f731fa92b63
Source dataset
uspto-grants-1982_06
Patent number
US04332800

Reaction notes

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