Water → HCID 14672333, compound

HRID 1194162Notes

Reaction equation

HRID 1194162 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:35](=[O:36])[N:13]3[C:14]([C:23]([O:25][CH2:26][C:27]4[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=4)=[O:24])=[C:15](OS(C)(=O)=O)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[SH-:37].[Na+].C(N(C(C)C)CC)(C)C.O>CN(C)C=O>[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:35](=[O:36])[N:13]3[C:14]([C:23]([O:25][CH2:26][C:27]4[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=4)=[O:24])=[C:15]([SH:37])[CH2:16][S:17][C@H:12]23)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 28015Sodium hydrosulfideHCID 81531DiisopropylethylamineHCID 14538788HCID 14538788, compound

Product 1

HCID 14672333HCID 14672333, compoundYield 49.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

(a-1) To a solution of 16.5 g (31.3 mM) of p-methoxybenzyl 7β-phenylacetamido-3-methanesulfonyloxy-3-cephem-4-carboxylate in 70 ml of N,N-dimethylformamide were added a solution of 2.75 g (34.4 mM) of 70% sodium hydrosulfide in 30 ml of N,N-dimethylformamide and 6.06 g (47.0 mM) of diisopropylethylamine at -20° C., and the mixture was stirred at 0° C. for one hour. After the reaction, 1 l of water was added, the mixture was washed with ethyl acetate (200 ml×3), and the aqueous layer was adjusted to pH 1 with 3% hydrochloric acid and extracted with ethyl acetate (500 ml and 200 ml). The extract was washed with a saturated aqueous sodium chloride solution (300 ml×2) and dried over anhydrous magnesium sulfate. The solvent was evaporated, the residue was dissolved in 200 ml of dichloromethane, and the solution was added dropwise to 700 ml of diethyl ether with stirring. The precipitate formed was collected by filtration to give 7.24 g of p-methoxybenzyl 7β-phenylacetamido-3-mercapto-3-cephem-4-carboxylate.

Workup

  1. additionwas added
  2. washthe mixture was washed with ethyl acetate (200 ml×3)
  3. extractionextracted with ethyl acetate (500 ml and 200 ml)
  4. washThe extract was washed with a saturated aqueous sodium chloride solution (300 ml×2)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. dissolutionthe residue was dissolved in 200 ml of dichloromethane
  8. additionthe solution was added dropwise to 700 ml of diethyl ether
  9. stirringwith stirring
  10. customThe precipitate formed
  11. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-928c77ed5fed4d95976e9a36e07934fd
Source dataset
uspto-grants-1989_03
Patent number
US04812562

Reaction notes

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