Sodium Bicarbonate → HCID 131713971, compound

HRID 986780Notes

Reaction equation

HRID 986780 reaction equation
ClCC([NH:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:43][O:44][CH3:45])[C:12]([NH:14][CH:15]2[C:41](=[O:42])[N:17]3[C:18]([C:25]([O:27][CH:28]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[O:26])=[C:19]([CH2:22][O:23][CH3:24])[CH2:20][S:21][C@H:16]23)=[O:13])[N:10]=1)=O.NC(N)=S.C(=O)(O)[O-].[Na+]>CC(N(C)C)=O>[NH2:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:43][O:44][CH3:45])[C:12]([NH:14][CH:15]2[C:41](=[O:42])[N:17]3[C:18]([C:25]([O:27][CH:28]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[O:26])=[C:19]([CH2:22][O:23][CH3:24])[CH2:20][S:21][C@H:16]23)=[O:13])[N:10]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2723790ThioureaHCID 131713972HCID 131713972, compound

Product 1

HCID 131713971HCID 131713971, compoundYield 35.6%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

200 mg of benzhydryl 7-[2-(2-chloroacetamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-methoxymethyl-3-cephem-4-carboxylate, followed by 45 mg of thiourea, were dissolved in 5 ml of dimethylacetamide. The solution was maintained at room temperature for 2 hours. after which a saturated aqueous solution of sodium bicarbonate was added. The reaction mixture was then extracted with 20 ml of ethyl acetate and the extract was washed with water to remove excess thiourea and then dried over anhydrous magnesium sulphate. After the drying agent had been filtered off, the filtrate was concentrated by evaporation under reduced pressure. The resulting residue was chromatographed through 30 g of silica gel (Wacogel C-100), eluted with ethyl acetate, to afford 63 mg of benzhydryl 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-methoxymethyl-3-cephem-4-carboxylate.

Workup

  1. extractionThe reaction mixture was then extracted with 20 ml of ethyl acetate
  2. washthe extract was washed with water
  3. customto remove excess thiourea
  4. dry with materialdried over anhydrous magnesium sulphate
  5. filtrationAfter the drying agent had been filtered off
  6. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  7. customThe resulting residue was chromatographed through 30 g of silica gel (Wacogel C-100)
  8. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-fb51967dbac347179a5f4450d05704dc
Source dataset
uspto-grants-1987_12
Patent number
US04716158

Reaction notes

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