(Trifluoromethyl)trimethylsilane → 8-(2-Chloro-benzenesulfonyl)-2-[4-(2,2,2-trifluoro-1-hydroxy-1-methyl-ethyl)-phenyl]-2,8-diaza-spiro[4.5]decan-1-one

HRID 2194138

반응식

HRID 2194138 반응식
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH2:13][C:12]3([CH2:19][CH2:18][N:17]([S:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[Cl:29])(=[O:22])=[O:21])[CH2:16][CH2:15]3)[C:11]2=[O:30])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[F:31][C:32]([Si](C)(C)C)([F:34])[F:33].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.Cl>[Cl:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[S:20]([N:17]1[CH2:18][CH2:19][C:12]2([C:11](=[O:30])[N:10]([C:7]3[CH:6]=[CH:5][C:4]([C:1]([OH:3])([CH3:2])[C:32]([F:34])([F:33])[F:31])=[CH:9][CH:8]=3)[CH2:14][CH2:13]2)[CH2:15][CH2:16]1)(=[O:22])=[O:21]

참가 물질

6

반응물 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 595779632-(4-Acetyl-phenyl)-8-(2-chloro-benzenesulfonyl)-2,8-diaza-spiro[4.5]decan-1-one2회

생성물 1

HCID 595780328-(2-Chloro-benzenesulfonyl)-2-[4-(2,2,2-trifluoro-1-hydroxy-1-methyl-ethyl)-phenyl]-2,8-diaza-spiro[4.5]decan-1-one수율 60.5%

시약·촉매·용매 2

HCID 313Hydrochloric Acid촉매HCID 8028Tetrahydrofuran용매

실험 절차

2-(4-Acetyl-phenyl)-8-(2-chloro-benzenesulfonyl)-2,8-diaza-spiro[4.5]decan-1-one (0.13 g), product of example 151), dissolved in THF (12 ml) under an argon atmosphere was treated at RT with (trifluoromethyl)trimethylsilane (0.062 g) then with tetra-n-butylammonium fluoride (1M solution in THF, 0.29 ml) and the reaction mixture was stirred overnight at RT. The mixture was made acidic with 3M aqueous HCl (a few drops) and stirred further 15 minutes. The solvent was removed in vacuo and the residue adsorbed on silica gel and chromatographed over silica gel (AcOEt/heptane, gradient from 0 to 40%) to give the desired product as white solid (0.091 g). MS (ESI): 517.1 MH+).

후처리

  1. customThe solvent was removed in vacuo
  2. customthe residue adsorbed on silica gel and chromatographed over silica gel (AcOEt/heptane, gradient from 0 to 40%)

출처 및 근거

ORD 기록
ord-0646c067664e4abd8f11a6ac87460ef8
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08329904B2

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