Diisopropylethylamine → HCID 46207474、化合物

HRID 2209343ノート

反応式

HRID 2209343 の反応式
[CH3:1][C:2]([CH3:22])=[CH:3][CH2:4][CH2:5]/[C:6](/[CH3:21])=[CH:7]/[CH2:8][CH2:9]/[C:10](/[CH3:20])=[CH:11]/[CH2:12][S:13][CH2:14][C@H:15]([NH2:19])[C:16]([OH:18])=[O:17].C(N(CC)C(C)C)(C)C.[CH2:32]([O:34][C:35](=[O:41])[CH2:36][CH2:37][N:38]=[C:39]=[O:40])[CH3:33]>C(Cl)Cl>[CH3:20]/[C:10](/[CH2:9][CH2:8]/[CH:7]=[C:6](\[CH3:21])/[CH2:5][CH2:4][CH:3]=[C:2]([CH3:22])[CH3:1])=[CH:11]\[CH2:12][S:13][CH2:14][C@@H:15]([C:16]([OH:18])=[O:17])[NH:19][C:39](=[O:40])[NH:38][CH2:37][CH2:36][C:35](=[O:41])[O:34][CH2:32][CH3:33]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 2733373Ethyl 3-isocyanatopropanoateHCID 6438372Farnesylcysteine

生成物 1

HCID 46207474HCID 46207474、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

S-trans, trans-Farnesyl-L-cysteine (325 mg, 1 mmol) and N,N-diisopropyl-ethyl-amine (650 mg, 5 mmol) were mixed in CH2Cl2 (10 mL). Ethyl-3-isocyanato-propionate (143, 1 mmol) was added to the reaction mixture. The reaction solution was stirred at room temperature overnight and the solvent was removed by rotary evaporation. The remaining residue was dissolved in ethyl acetate (100 mL) and washed with 1 N HCl solution (50 mL×2). The ethyl acetate solution was dried over Na2SO4 and concentrated to a crude reaction mixture. The resulting mixture was purified by HPLC (200 mg, 43%) to yield Compound D. 1H-NMR (500 MHz, MeOH-d4): δ 1.28 (t, J=7.5 Hz, 3H), 1.62 (s, 3H), 1.63 (s, 3H), 1.69 (s, 3H), 1.70 (s, 3H), 1.98 (m, 2H), 2.06 (m, 6H), 2.52 (t, J=6.5, 2H), 2.79 (dd, J=7.0, 14.0 Hz, 1H), 2.93 (dd, J=4.5, 13.5 Hz, 1H), 3.17 (dd, J=7.5, 13.5 Hz, 1H), 3.28 (dd, J=8.5, 13.5 Hz, 1H), 3.41 (t, J=6.5 Hz, 3H), 4.16 (q, J=7.5 Hz, 2H), 4.50 (dd, J=4.5, 6.5 Hz, 1H), 5.11 (m, 2H), 5.23 (t, J=7.5, 1H). 13C-NMR (125 MHz, MeOH-d4): δ 14.6, 16.1, 16.2, 17.8, 26.0, 27.4, 27.8, 30.5, 34.4, 35.9, 36.7, 40.8, 40.9, 54.0, 61.7, 121.7, 125.1, 125.5, 132.1, 136.3, 140.5, 160.2, 173.8, 175.0; ES-MS: mass calcd for Chemical Formula: C24H40N2O5S 468.7. Found (M+Na) m/z 491.3.

後処理

  1. customthe solvent was removed by rotary evaporation
  2. dissolutionThe remaining residue was dissolved in ethyl acetate (100 mL)
  3. washwashed with 1 N HCl solution (50 mL×2)
  4. dry with materialThe ethyl acetate solution was dried over Na2SO4
  5. concentrationconcentrated to a crude
  6. customreaction mixture
  7. customThe resulting mixture was purified by HPLC (200 mg, 43%)

出典と根拠

ORDレコード
ord-56ef1846750a43d58b32171884d6bb9c
出典データセット
uspto-grants-2016_06
特許番号
US09376383B2

反応ノート

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