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 dihydrate

HRID 1155661Notes

Reaction equation

HRID 1155661 reaction equation
CC(C)=[O:3].C([O:7]N=C(C1N=C(N)SN=1)C(NC1C(=O)N2C(C([O-])=O)=C(C[N+]3C=CC=CC=3)CS[C@H]12)=O)C.[CH2:38]([O:40][N:41]=[C:42]([C:65]1[N:69]=[C:68]([NH2:70])[S:67][N:66]=1)[C:43]([NH:45][CH:46]1[C:63](=[O:64])[N:48]2[C:49]([C:60]([O-:62])=[O:61])=[C:50]([CH2:53][N+:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)[CH2:51][S:52][C@H:47]12)=[O:44])[CH3:39]>O>[OH2:3].[OH2:7].[CH2:38]([O:40][N:41]=[C:42]([C:65]1[N:69]=[C:68]([NH2:70])[S:67][N:66]=1)[C:43]([NH:45][CH:46]1[C:63](=[O:64])[N:48]2[C:49]([C:60]([O-:62])=[O:61])=[C:50]([CH2:53][N+:54]3[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=3)[CH2:51][S:52][C@H:47]12)=[O:44])[CH3:39]

Participants

4

Reactant 2

HCID 1317127487-[2-Ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate acetoneHCID 1317127507-[2-Ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate

Product 1

HCID 1317127517-[2-Ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate dihydrate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 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) (40 g) in water (50 ml) was added a small amount of colorless needles of 7-[2-ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate (syn isomer) and the mixture was stirred for one hour in an ice bath. The resulting precipitates were collected by filtration, washed with cold water (33 ml) and dried in vacuo for 10 hours to give 7-[2-ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate dihydrate (syn isomer) (24.7 g), as colorless needles, mp 170° to 175° C. (dec.).

Workup

  1. customThe resulting precipitates
  2. filtrationwere collected by filtration
  3. washwashed with cold water (33 ml)
  4. customdried in vacuo for 10 hours

Sources & evidence

ORD record
ord-4df573e885ab434cbdf1f7da23e3d6cb
Source dataset
uspto-grants-1982_06
Patent number
US04332800

Reaction notes

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