Sodium Chloride → HCID 131714454, compound

HRID 638083Notes

Reaction equation

HRID 638083 reaction equation
Br[CH2:2][C:3](=O)[C:4](=[N:35][OH:36])[C:5]([NH:7][CH:8]1[C:33](=[O:34])[N:10]2[C:11]([C:17]([O:19][CH:20]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])=[C:12]([CH:15]=[CH2:16])[CH2:13][S:14][C@H:9]12)=[O:6].[NH2:38][C:39]([NH2:41])=[S:40].C(=O)(O)[O-].[Na+].[Cl-].[Na+]>CN(C)C(=O)C>[NH2:41][C:39]1[S:40][CH:2]=[C:3]([C:4](=[N:35][OH:36])[C:5]([NH:7][CH:8]2[C:33](=[O:34])[N:10]3[C:11]([C:17]([O:19][CH:20]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[O:18])=[C:12]([CH:15]=[CH2:16])[CH2:13][S:14][C@H:9]23)=[O:6])[N:38]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 516892Sodium BicarbonateHCID 2723790ThioureaHCID 178436960HCID 178436960, compound

Product 1

HCID 131714454HCID 131714454, compoundYield 36.6%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of benzhydryl 7-(4-bromo-2-hydroxyiminoacetoacetamido)-3-vinyl-3-cephem-4-carboxylate (48 g) in N,N-dimethylacetamide (200 ml) was added thiourea (7.0 g) at 5° C., and the mixture was stirred at ambient temperature for an hour. After the reaction mixture was poured into 3% aqueous sodium bicarbonate (2 liter), sodium chloride (150 g) was added thereto. The precipitates were collected by filtration and then dissolved in a mixture of acetone (200 ml) and ethyl acetate (500 ml). The separated organic layer was washed with an aqueous sodium chloride, followed by evaporation. The resultant precipitates were collected by filtration, washed with ethyl acetate and diethyl ether and dried in vacuo to give benzhydryl 7-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylate (syn isomer) (16.9 g), mp 133°-136° C.

Workup

  1. additionwas added
  2. filtrationThe precipitates were collected by filtration
  3. dissolutiondissolved in a mixture of acetone (200 ml) and ethyl acetate (500 ml)
  4. washThe separated organic layer was washed with an aqueous sodium chloride
  5. customfollowed by evaporation
  6. customThe resultant precipitates
  7. filtrationwere collected by filtration
  8. washwashed with ethyl acetate and diethyl ether
  9. customdried in vacuo

Sources & evidence

ORD record
ord-535270cd81eb41f0961af10d2eaec98a
Source dataset
uspto-grants-1985_12
Patent number
US04559334

Reaction notes

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