Sulfuric Acid → HCID 131717271, compound

HRID 1030050Notes

Reaction equation

HRID 1030050 reaction equation
[CH2:1]([O:4][N:5]=[C:6]([C:29]1[N:33]=[C:32]([NH2:34])[S:31][N:30]=1)[C:7]([NH:9][CH:10]1[C:27](=[O:28])[N:12]2[C:13]([C:24]([O-:26])=[O:25])=[C:14]([CH2:17][N+:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:15][S:16][C@H:11]12)=[O:8])[CH:2]=[CH2:3].C(O)(C)C.[S:39](=[O:43])(=[O:42])([OH:41])[OH:40]>>[S:39]([O-:43])([O-:42])(=[O:41])=[O:40].[CH2:1]([O:4][N:5]=[C:6]([C:29]1[N:33]=[C:32]([NH2:34])[S:31][N:30]=1)[C:7]([NH:9][CH:10]1[C:27](=[O:28])[N:12]2[C:13]([C:24]([OH:26])=[O:25])=[C:14]([CH2:17][N+:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:15][S:16][C@H:11]12)=[O:8])[CH:2]=[CH2:3].[CH2:1]([O:4][N:5]=[C:6]([C:29]1[N:33]=[C:32]([NH2:34])[S:31][N:30]=1)[C:7]([NH:9][CH:10]1[C:27](=[O:28])[N:12]2[C:13]([C:24]([OH:26])=[O:25])=[C:14]([CH2:17][N+:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:15][S:16][C@H:11]12)=[O:8])[CH:2]=[CH2:3]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 131717273HCID 131717273, compound

Product 1

HCID 131717271HCID 131717271, compound

Procedure

7-[2-allyloxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)-acetamido]-3-(1-pyridinio)methyl-3-cephem-4-carboxylate (syn isomer) (5 g) was dissolved in 1 M sulfuric acid (5 ml) at ambient temparature. Isopropyl alcohol (50 ml) was added to the mixture. The mixture was stirred for 2 hours at ambient temparature. The precipitated crystals were collected by filtration, washed with isopropyl alcohol, and dried over phosphorus pentoxide in vacuo to give the crystals of 7-[2-allyloxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-(1-pyridinio)methyl-3-cephem-4-carboxylate hemisulfate (solvate of 1/2 isopropyl alcohol) (syn isomer) (5 g).

Workup

  1. filtrationThe precipitated crystals were collected by filtration
  2. washwashed with isopropyl alcohol
  3. dry with materialdried over phosphorus pentoxide in vacuo

Sources & evidence

ORD record
ord-c08d1f17802f448eb23872938cda2400
Source dataset
uspto-grants-1992_04
Patent number
US05104866

Reaction notes

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