Pyridine → (2S)-2-(4-chloro-benzenesulfonylamino)-5,5,5-trifluoro-3-(2,2,2-trifluoroethyl)pentanoic acid methyl ester

HRID 1987567ノート

反応式

HRID 1987567 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:12][O:13][C:14](=[O:28])[C@@H:15]([NH2:27])[CH:16]([CH2:22][C:23]([F:26])([F:25])[F:24])[CH2:17][C:18]([F:21])([F:20])[F:19].N1C=CC=CC=1>C(Cl)Cl>[CH3:12][O:13][C:14](=[O:28])[C@@H:15]([NH:27][S:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9])[CH:16]([CH2:17][C:18]([F:21])([F:20])[F:19])[CH2:22][C:23]([F:25])([F:26])[F:24]

参加物

5

反応物 3

HCID 1049PyridineHCID 73984-Chlorobenzenesulfonyl chlorideHCID 25112112(2S)-2-amino-5,5,5-trifluoro-3-(2,2,2-trifluoroethyl)-pentanoic acid methyl ester

生成物 1

HCID 25112113(2S)-2-(4-chloro-benzenesulfonylamino)-5,5,5-trifluoro-3-(2,2,2-trifluoroethyl)pentanoic acid methyl ester収率 86%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
25 °C

実験手順

4-Chlorophenyl sulphonyl chloride (211 mg, 1.00 mmol) was added to a solution of (2S)-2-amino-5,5,5-trifluoro-3-(2,2,2-trifluoroethyl)-pentanoic acid methyl ester (267 mg, 1.00 mmol) and pyridine (0.45 mL, 3.00 mmol) in CH2Cl2 (5 mL) and the reaction was subsequently stirred for 18 h at 25° C. The solvent was removed in vacuo and the residue was dissolved in EtOAc (20 mL). This solution was washed with 1M HCl (2×10 mL) and brine (10 mL), dried over Na2SO4 and evaporated to afford a crude oil which was purified by flash chromatography eluting with 20:80 EtOAc:hexanes to provide the title compound (380 mg) as an oil in 86% yield. Mass Spectrum (−ESI): 446.0 [M−H]−.

後処理

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in EtOAc (20 mL)
  3. washThis solution was washed with 1M HCl (2×10 mL) and brine (10 mL)
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customto afford a crude oil which
  7. customwas purified by flash chromatography
  8. washeluting with 20:80 EtOAc

出典と根拠

ORDレコード
ord-96fe88b2d96049779859bf9515005883
出典データセット
uspto-grants-2009_06
特許番号
US07550629B2

反応ノート

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