Hydrochloric Acid → 7beta-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-carboxy-1-methylethoxyimino)acetamido]-3-{N,N-dimethyl-N-{(5-hydroxy-4-oxo-1,4-dihydropyridin-2-yl)methyl}ammonio]methyl-3-cephem-4-carboxylate hydrochloride

HRID 5532Notes

Reaction equation

HRID 5532 reaction equation
[ClH:1].[NH2:2][C:3]1[S:7][N:6]=[C:5]([C:8](=[N:37][O:38][C:39]([C:42]([OH:44])=[O:43])([CH3:41])[CH3:40])[C:9]([NH:11][C@@H:12]2[C:35](=[O:36])[N:14]3[C:15]([C:32]([O-:34])=[O:33])=[C:16]([CH2:19][N+:20]([CH3:31])([CH3:30])[CH2:21][C:22]4[NH:23][CH:24]=[C:25]([OH:29])[C:26](=[O:28])[CH:27]=4)[CH2:17][S:18][C@H:13]23)=[O:10])[N:4]=1>>[ClH:1].[NH2:2][C:3]1[S:7][N:6]=[C:5]([C:8](=[N:37][O:38][C:39]([C:42]([OH:44])=[O:43])([CH3:41])[CH3:40])[C:9]([NH:11][C@@H:12]2[C:35](=[O:36])[N:14]3[C:15]([C:32]([O-:34])=[O:33])=[C:16]([CH2:19][N+:20]([CH3:30])([CH3:31])[CH2:21][C:22]4[NH:23][CH:24]=[C:25]([OH:29])[C:26](=[O:28])[CH:27]=4)[CH2:17][S:18][C@H:13]23)=[O:10])[N:4]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 1317181237beta-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-carboxy-1-methylethoxyimino)acetamido]-3-[N,N-dimethyl-N-((5-hydroxy-4-oxo-1,4-dihydropyridin-2-yl)methyl}ammonio]methyl-3-cephem-4-carboxylate

Product 1

HCID 1317181547beta-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-carboxy-1-methylethoxyimino)acetamido]-3-{N,N-dimethyl-N-{(5-hydroxy-4-oxo-1,4-dihydropyridin-2-yl)methyl}ammonio]methyl-3-cephem-4-carboxylate hydrochloride

Procedure

To 1N hydrochloric acid was added 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-carboxy-1-methylethoxyimino)acetamido]-3-[N,N-dimethyl-N-((5-hydroxy-4-oxo-1,4-dihydropyridin-2-yl)methyl}ammonio]methyl-3-cephem-4-carboxylate (syn isomer) (2.2 g). The mixture was stirred under ice-cooling for 3 hours. The resulting precipitate was collected by filtration, washed with a small amount of cold water and dried under reduced pressure to give 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-carboxy-1-methylethoxyimino)acetamido]-3-{N,N-dimethyl-N-{(5-hydroxy-4-oxo-1,4-dihydropyridin-2-yl)methyl}ammonio]methyl-3-cephem-4-carboxylate hydrochloride (syn isomer) (1.1 g).

Workup

  1. temperaturecooling for 3 hours
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with a small amount of cold water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-470255b2b67b486898084bd101cb65db
Source dataset
uspto-grants-1993_09
Patent number
US05244890

Reaction notes

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