Hydrochloric Acid → HCID 131714639, compound

HRID 2413810Notes

Reaction equation

HRID 2413810 reaction equation
[CH2:1]([O:3][N:4]=[C:5]([C:33]1[N:37]=[C:36]([NH2:38])[S:35][N:34]=1)[C:6]([NH:8][CH:9]1[C:31](=[O:32])[N:11]2[C:12]([C:28]([OH:30])=[O:29])=[C:13]([CH:16]=[CH:17][S:18][C:19]3[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][N:20]=3)[CH2:14][S:15][C@H:10]12)=[O:7])[CH3:2].S(S([O-])=O)([O-])=O.[Na+].[Na+].Cl>C(=O)(O)[O-].[Na+]>[CH2:1]([O:3][N:4]=[C:5]([C:33]1[N:37]=[C:36]([NH2:38])[S:35][N:34]=1)[C:6]([NH:8][CH:9]1[C:31](=[O:32])[N:11]2[C:12]([C:28]([OH:30])=[O:29])=[C:13]([CH:16]=[CH:17][S:18][C:19]3[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][N:20]=3)[CH2:14][S:15][C@H:10]12)=[O:7])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24489Sodium DithioniteHCID 131714640HCID 131714640, compound

Product 1

HCID 131714639HCID 131714639, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

To an ice-cooled solution of 7-[2-ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-[2-(5-nitro-2-pyridyl)thiovinyl]-3-cephem-4-carboxylic acid (syn isomer) (trans isomer) (1.35 g) in an aqueous solution of sodium bicarbonate (30 ml) was added sodium hydrosulfite (4.05 g) under stirring. The mixture was stirred for 30 minutes at room temperature and cooled in an ice-bath and acidified to pH 3.5 with 10% hydrochloric acid. The precipitate was collected, washed and dried to give 1.05 g of 7-[2-ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-[2-(5-amino-2-pyridyl)thiovinyl)-3-cephem-4-carboxylic acid (syn isomer) (trans isomer).

Workup

  1. stirringThe mixture was stirred for 30 minutes at room temperature
  2. temperaturecooled in an ice-bath
  3. customThe precipitate was collected
  4. washwashed
  5. customdried

Sources & evidence

ORD record
ord-6057894630ec4fde9bb02a2b4d2c5c83
Source dataset
uspto-grants-1988_01
Patent number
US04719206

Reaction notes

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