Hydrochloric Acid → HCID 131714639, compound

HRID 1380971Notes

Reaction equation

HRID 1380971 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-da11e9217d824d43bdebcfb4251596b2
Source dataset
uspto-grants-1986_04
Patent number
US04584290

Reaction notes

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