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 647245Notes

Reaction equation

HRID 647245 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-bf06f87d5ac64a15bce7d792469d7ebf
Source dataset
uspto-grants-1983_10
Patent number
US04408042

Reaction notes

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