Cyclohexanecarboxylic acid → Tert-butyl 3-(3-(cyclohexanecarboxamido)phenyl)propylcarbamate

HRID 1189930ノート

反応式

HRID 1189930 の反応式
[CH:1]1([C:7]([OH:9])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)C(C)C)C.C1(C[NH:48][C:49]2[CH:50]=[C:51]([CH2:55][CH2:56][CH2:57][NH:58][C:59](=[O:65])[O:60][C:61]([CH3:64])([CH3:63])[CH3:62])[CH:52]=[CH:53][CH:54]=2)CCCCC1>CN(C=O)C.O>[CH:1]1([C:7]([NH:48][C:49]2[CH:50]=[C:51]([CH2:55][CH2:56][CH2:57][NH:58][C:59](=[O:65])[O:60][C:61]([CH3:63])([CH3:62])[CH3:64])[CH:52]=[CH:53][CH:54]=2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

参加物

7

反応物 4

HCID 7413Cyclohexanecarboxylic acidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 59317002Tert-butyl 3-(3-(cyclohexylmethylamino)phenyl)propylcarbamate

生成物 1

HCID 59316922Tert-butyl 3-(3-(cyclohexanecarboxamido)phenyl)propylcarbamate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

To a mixture of cyclohexanecarboxylic acid (21) (0.23 ml, 1.79 mmol), TBTU (0.56 g, 1.74 mmol) and iPr2EtN (0.33 ml, 1.89 mmol) in DMF (20 ml) was added tert-butyl 3-(3-(cyclohexylmethylamino)phenyl)propylcarbamate (17) (0.40 g, 1.59 mmol) in DMF (5 ml). The mixture was stirred at room temperature for 18 h and then diluted with water. The solution was extracted with ethyl acetate and the combined extracts were washed with water, aqueous NaHCO3 and brine, dried over Na2SO4 and concentrated under reduced pressure. Purification by flash chromatography (5 to 50% EtOAc-hexanes gradient) gave tert-butyl 3-(3-(cyclohexanecarboxamido)phenyl)propylcarbamate (22) as a colorless oil. Yield (0.455 g, 78%); Yield (0.2 g, 32%); 1H NMR (400 MHz, CDCl3) δ 7.43 (br s, 1H), 7.26-7.28 (m, 2H), 7.20 (t, J=7.6 Hz, 1H), 7.08 (br s, 1H), 6.89-6.91 (m, 1H), 3.12 (t, J=6.0 Hz, 2H), 2.61 (t, J=8.4 Hz, 2H), 2.17-2.23 (m, 1H), 1.93-1.96 (m, 2H), 1.74-1.86 (m, 3H), 1.65-1.72 (m, 2H), 1.48-1.59 (m, 1H), 1.31-1.42 (m, 2H), 1.43 (s, 9H), 1.22-1.38 (m, 4H).

後処理

  1. extractionThe solution was extracted with ethyl acetate
  2. washthe combined extracts were washed with water, aqueous NaHCO3 and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash chromatography (5 to 50% EtOAc-hexanes gradient)

出典と根拠

ORDレコード
ord-ba9174da36814b1fb6d4cfa62d16058f
出典データセット
uspto-grants-2014_03
特許番号
US08674137B2

反応ノート

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