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

HRID 23586ノート

反応式

HRID 23586 の反応式
[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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-8d10b99ddfb74c7997f0e0c5aead1b08
出典データセット
uspto-grants-2005_02
特許番号
US06852713B2

反応ノート

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