Diisopropylethylamine → HCID 46207474, compound

HRID 2209343Notes

Reaction equation

HRID 2209343 reaction equation
[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]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2733373Ethyl 3-isocyanatopropanoateHCID 6438372Farnesylcysteine

Product 1

HCID 46207474HCID 46207474, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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%)

Sources & evidence

ORD record
ord-56ef1846750a43d58b32171884d6bb9c
Source dataset
uspto-grants-2016_06
Patent number
US09376383B2

Reaction notes

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