Potassium Carbonate → tert-Butyl (4-{[4-(trifluoromethyl)phenyl]thio}cyclohexyl)carbamate

HRID 2239591

反応式

HRID 2239591 の反応式
CS(O[CH:6]1[CH2:11][CH2:10][CH:9]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8][CH2:7]1)(=O)=O.[F:20][C:21]([F:30])([F:29])[C:22]1[CH:27]=[CH:26][C:25]([SH:28])=[CH:24][CH:23]=1.C([O-])([O-])=O.[K+].[K+]>C1COCC1.O>[F:30][C:21]([F:20])([F:29])[C:22]1[CH:23]=[CH:24][C:25]([S:28][CH:6]2[CH2:7][CH2:8][CH:9]([NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:10][CH2:11]2)=[CH:26][CH:27]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 1366534-(Trifluoromethyl)thiophenolHCID 21882613trans-4-(Boc-amino)cyclohexyl methanesulfonate

生成物 1

HCID 86625880tert-Butyl (4-{[4-(trifluoromethyl)phenyl]thio}cyclohexyl)carbamate収率 43%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
130 °C

実験手順

4-[(tert-Butoxycarbonyl)amino]cyclohexyl methanesulfonate (0.7 g, 2.39 mmol), 4-(trifluoromethyl)thiophenol (1.28 g, 7.16 mmol) and K2CO3 (1.32 g, 9.54 mmol) was dissolved in THF (21 ml) and the reaction mixture was heated in a microwave reactor at 130° C. for 30 mins. The reaction mixture was diluted with water (300 ml) and extracted with EtOAc (2×150 ml). The combined organic phases were dried over Na2SO4, filtrated and evaporated. The residue was purified by silica gel column chromatography using a 85:15 mixture of heptane:EtOAc to give the title compound (0.386 g, 43%) as a 50:50 mixture of cis and trans isomers. 1H-NMR (CDCl3, 500 MHz): δ 7.55-7.50 (m, 4H), 7.45-7.40 (m, 4H), 4.70-4.23 (m, 2H), 3.69-3.36 (m, 3H), 3.16-3.05 (m, 1H), 2.13-2.04 (m, 4H), 1.95-1.64 (m, 9H), 1.54-1.40 (m, 1H), 1.45 (ds, 18H), 1.30-1.15 (m, 2H); 13C-NMR (CDCl3, 125 MHz): δ 155.4, 141.1, 140.7, 130.5, 129.9, 128.6, 128.5, 128.2, 126.0, 125.9, 125.9, 125.9, 125.4, 123.2, 79.5, 49.1, 47.9, 44.8, 43.8, 33.4, 32.0, 29.2, 29.1, 28.6.

後処理

  1. extractionextracted with EtOAc (2×150 ml)
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. filtrationfiltrated
  4. customevaporated
  5. customThe residue was purified by silica gel column chromatography
  6. additiona 85:15 mixture of heptane

出典と根拠

ORDレコード
ord-b6a4b62dec7b47049eaeb0c993d48acd
出典データセット
uspto-grants-2010_05
特許番号
US07723333B2

関連ノート

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