Water → 2-Allylamino-1-[3-(S)-(tert-butyl-dimethyl-silanyloxy)-pyrrolidin-1-yl]-2-(S)-phenyl-ethanone

HRID 23586Notes

Reaction equation

HRID 23586 reaction equation
[CH2:1]([N:4]([C@@H:17]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:18]([N:20]1[CH2:24][CH2:23][C@H:22]([O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])[CH2:21]1)=[O:19])S(C1C=CC=CC=1[N+]([O-])=O)(=O)=O)[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+].C1(S)C=CC=CC=1.O>CN(C)C=O>[CH2:1]([NH:4][C@@H:17]([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:18]([N:20]1[CH2:24][CH2:23][C@H:22]([O:25][Si:26]([C:29]([CH3:31])([CH3:32])[CH3:30])([CH3:27])[CH3:28])[CH2:21]1)=[O:19])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 962WaterHCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 20756544N-Allyl-N-{2-[3-(S)-(tert-butyl-dimethyl-silanyloxy)-pyrrolidin-1-yl]-2-oxo-1-(S)-phenyl-ethyl}-2-nitro-benzenesulfonamide

Product 1

HCID 207565402-Allylamino-1-[3-(S)-(tert-butyl-dimethyl-silanyloxy)-pyrrolidin-1-yl]-2-(S)-phenyl-ethanoneYield 97.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution N-allyl-N-{2-[3-(S)-(tert-butyl-dimethyl-silanyloxy)-pyrrolidin-1-yl]-2-oxo-1-(S)-phenyl-ethyl}-2-nitro-benzenesulfonamide (8.73 g, 15.6 mmol) in anhydrous dimethylformamide (45 cm3) was added potassium carbonate (6.50 g, 46.8 mmol). The mixture was stirred at ambient temperature for 10 minutes and thiophenol (2.25 cm3, 21.8 mmol) was added dropwise over 10 minutes. The mixture was stirred for 16 hours at ambient temperature and poured into water (500 cm3) and extracted with ethyl acetate (3×150 cm3). The combined ethyl acetate extracts were washed with water (2×100 cm3), brine (1×100 cm3), dried over sodium sulfate, vacuum filtered and the volatile fractions removed in vacuo to a foul smelling yellow oil. The crude product was purified by column chromatography (silica, eluting with hexane-ethyl acetate 1:1 to 0:1) to afford the title compound as a yellow viscous oil (5.67 g, 97.1%) with a positive ion ESI (M+H)+375.2.

Workup

  1. stirringThe mixture was stirred for 16 hours at ambient temperature
  2. extractionextracted with ethyl acetate (3×150 cm3)
  3. washThe combined ethyl acetate extracts were washed with water (2×100 cm3), brine (1×100 cm3)
  4. dry with materialdried over sodium sulfate, vacuum
  5. filtrationfiltered
  6. customthe volatile fractions removed in vacuo to a foul smelling yellow oil
  7. customThe crude product was purified by column chromatography (silica, eluting with hexane-ethyl acetate 1:1 to 0:1)

Sources & evidence

ORD record
ord-8d10b99ddfb74c7997f0e0c5aead1b08
Source dataset
uspto-grants-2005_02
Patent number
US06852713B2

Reaction notes

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