Sodium hydride → HCID 57266598, compound

HRID 744888Notes

Reaction equation

HRID 744888 reaction equation
[C:1]([OH:9])(=[S:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[C:12]([O:16][C:17]([N:19]1[CH2:23][C@H:22](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:21][C@H:20]1[C:35]([O:37][CH2:38][CH3:39])=[O:36])=[O:18])([CH3:15])([CH3:14])[CH3:13]>CN(C)C=O.[I-].[Na+]>[C:12]([O:16][C:17]([N:19]1[CH2:23][C@@H:22]([S:8][C:1](=[O:9])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:21][C@H:20]1[C:35]([O:37][CH2:38][CH3:39])=[O:36])=[O:18])([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 57114913HCID 57114913, compoundHCID 178526132HCID 178526132, compound

Product 1

HCID 57266598HCID 57266598, compoundYield 70.5%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

Next, 36.4 g of thiobenzoic acid was dissolved in 300 ml of dimethylformamide and cooled on an ice bath, to which was subsequently added 10.5 g of sodium hydride. To this were added 102 g of (2S,4R)-1-(t-butoxycarbonyl)-2-ethoxycarbonyl -4-(p-toluenesulfonyloxy)pyrrolidine dissolved in 200 ml of dimethylformamide and 37.5 g of sodium iodide, followed by heating at 80° C. for 3 hours. After concentration of the reaction mixture, the thus obtained residue was dissolved in .benzene, and the resulting organic layer was washed with 5% sodium bicarbonate aqueous solution, 10% citric acid aqueous solution and water in that order, followed by drying over sodium sulfate and subsequent evaporation of the solvent under a reduced pressure. The resulting residue was purified by a silica gel column chromatography to yield 66 g of (2S,4S)-1-(t-butoxycarbonyl)-2-ethoxycarbonyl -4-benzoylthiopyrrolidine.

Workup

  1. temperaturecooled on an ice bath, to which
  2. dissolutionAfter concentration of the reaction mixture, the thus obtained residue was dissolved in
  3. washbenzene, and the resulting organic layer was washed with 5% sodium bicarbonate aqueous solution, 10% citric acid aqueous solution and water in that order
  4. dry with materialby drying over sodium sulfate and subsequent evaporation of the solvent under a reduced pressure
  5. customThe resulting residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-f7b80768ff7d46eebdd05d5ea9a31630
Source dataset
uspto-grants-1996_09
Patent number
US05559224

Reaction notes

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