Triethylamine → HCID 71279909、化合物

HRID 246161ノート

反応式

HRID 246161 の反応式
[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([C:14](=O)[NH2:15])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O>ClCCl.O>[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([C:14]#[N:15])[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 71279990HCID 71279990、化合物

生成物 1

HCID 71279909HCID 71279909、化合物収率 87%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-10 °C

実験手順

In a 25 mL round bottomed flask (cis-3-carbamoyl-cyclohexyl)-carbamic acid tert-butyl ester (1.00 g, 4.13 mmol) was suspended in dichlormethane (7 mL). The suspension was cooled to −10° C. in an acetone-dry ice bath. To the cooled suspension was added slowly triethylamine (1.15 mL, 8.25 mmol) and subsequently TFAA (0.62 mL, 4.39 mmol) so that the temperature is maintained. The reaction mixture was stirred at that temperature for 3 h and then diluted with water and dichloromethane. The organic layer was washed with water, dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 0% to 60% EtOAc in heptane) to afford 0.803 g (87%) of cis-(3-cyano-cyclohexyl)-carbamic acid tert-butyl ester as a white crystalline solid. 1H NMR (300 MHz, DMSO-d6) δ: 6.86 (d, J=7.9 Hz, 1H), 3.09-3.30 (m, 1H), 2.77 (tt, J=12.0, 3.3 Hz, 1H), 2.04 (d, J=12.1 Hz, 1H), 1.90 (d, J=9.1 Hz, 1H), 1.61-1.80 (m, 2H), 1.37 (s, 9H), 1.21-1.35 (m, 3H), 0.98-1.20 (m, 1H).

後処理

  1. temperatureis maintained
  2. washThe organic layer was washed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by flash chromatography (silica gel, 0% to 60% EtOAc in heptane)

出典と根拠

ORDレコード
ord-b314fd5289e549de8e86bb6ada1dc50d
出典データセット
uspto-grants-2014_02
特許番号
US08658646B2

反応ノート

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