Sulfuric Acid → HCID 131717693, compound

HRID 1681664Notes

Reaction equation

HRID 1681664 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7](=[N:33][O:34][C:35]([C:38]([OH:40])=[O:39])([CH3:37])[CH3:36])[C:8]([NH:10][C@@H:11]2[C:31](=[O:32])[N:13]3[C:14]([C:28]([O-:30])=[O:29])=[C:15]([CH2:18][N+:19]4[N:23]5[CH2:24][CH2:25][CH2:26][NH:27][C:22]5=[CH:21][CH:20]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:3]=1.[S:41](=[O:45])(=[O:44])([OH:43])[OH:42]>C(#N)C>[S:41]([OH:45])([O-:44])(=[O:43])=[O:42].[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7](=[N:33][O:34][C:35]([C:38]([OH:40])=[O:39])([CH3:36])[CH3:37])[C:8]([NH:10][C@@H:11]2[C:31](=[O:32])[N:13]3[C:14]([C:28]([OH:30])=[O:29])=[C:15]([CH2:18][N+:19]4[N:23]5[CH2:24][CH2:25][CH2:26][NH:27][C:22]5=[CH:21][CH:20]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:3]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 131717695HCID 131717695, compound

Product 1

HCID 131717693HCID 131717693, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 7β-(2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-carboxy-1-methylethoxyimino)acetamido]-3-(4,5,6,7-tetrahydro-1-pyrazolo[1,5-a]pyrimidinio)methyl-3-cephem-4-carboxylate (syn isomer)(0.5 g) in acetonitrile (1 ml) was added 2M sulfuric acid (0.5 ml) at ambient temperature. The mixture was stirred for 30 minutes. The resulting precipitate was collected by filtration to give 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-carboxy-1-methylethoxyimino)acetamido]-3-(4,5,6,7-tetrahydro-1-pyrazolo[1,5-a]-pyrimidinio)methyl-3-cephem-4-carboxylate sulfate (syn isomer) as crystals (380 mg).

Workup

  1. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-0e67787dd97349ffbbeea733c537fb16
Source dataset
uspto-grants-1992_12
Patent number
US05173485

Reaction notes

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