Diisopropylethylamine → HCID 46208101, compound

HRID 1482463Notes

Reaction equation

HRID 1482463 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH2:6][CH2:7][N:8]=[C:9]=[S:10])=[O:5].[CH3:11][C:12]([CH3:32])=[CH:13][CH2:14][CH2:15]/[C:16](/[CH3:31])=[CH:17]/[CH2:18][CH2:19]/[C:20](/[CH3:30])=[CH:21]/[CH2:22][S:23][CH2:24][C@H:25]([NH2:29])[C:26]([OH:28])=[O:27].C(N(CC)C(C)C)(C)C>C1COCC1.C(OCC)(=O)C>[CH2:2]([O:3][C:4](=[O:5])[CH2:6][CH2:7][NH:8][C:9](=[S:10])[NH:29][C@@H:25]([CH2:24][S:23][CH2:22]/[CH:21]=[C:20](\[CH3:30])/[CH2:19][CH2:18]/[CH:17]=[C:16](\[CH3:31])/[CH2:15][CH2:14][CH:13]=[C:12]([CH3:32])[CH3:11])[C:26]([OH:28])=[O:27])[CH3:1]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 526514Ethyl 3-isothiocyanatopropionateHCID 6438372Farnesylcysteine

Product 1

HCID 46208101HCID 46208101, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a 100 mL round bottom flask, to a suspension of ethyl-3-isothiocynato propionate (159 mg, 1 mmol) and S-trans, trans-farnesyl-L-cysteine (325 mg, 1 mmol) in THF (5 mL) was added N,N-diisopropyl-ethyl-amine (0.87 mL, 5 mmol) dropwise. The solution was stirred at room temperature overnight. The mixture was diluted with ethyl acetate (60 mL) and washed by 0.5 N HCl (10 mL×1), H2O (10 mL×1) and brine (10 mL×1). The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified by preparative HPLC (220 mg, 45%) to yield Compound F. 1H-NMR (500 MHz, CD3OD): δ 1.17 (t, J=5.0 Hz, 3H), 1.50 (s, 3H), 1.51 (s, 3H), 1.57 (s, 3H), 1.59 (s, 3H), 1.86-2.06 (m, 8H), 2.54 (t, J=5.0 Hz, 2H), 2.77 (dd, J=5.0, 15.0 Hz, 1H), 2.95-2.96 (m, 1H), 3.05-3.06 (m, 1H), 3.16-3.20 (m, 1H), 3.68 (broad, 2H), 4.06 (q, J=5.0 Hz, 2 H), 5.00-5.01 (m, 2H), 5.09-5.14 (m, 2H). 13C-NMR (125 MHz, CD3OD): δ 14.65, 16.19, 16.31, 17.83, 25.97, 27.39, 27.80, 30.70, 33.22, 33.91, 34.80, 40.80, 40.90, 57.89, 61.03, 61.71, 61.93, 121.35, 121.70, 125.16, 132.11, 136.24, 140.52, 173.76, 174.47, 210.16; ES-MS: mass calcd for Chemical Formula: C24H40N2O4S2 484.72. Found (M+) m/z 485.3, (M+Na) m/z 507.3.

Workup

  1. washwashed by 0.5 N HCl (10 mL×1), H2O (10 mL×1) and brine (10 mL×1)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by preparative HPLC (220 mg, 45%)

Sources & evidence

ORD record
ord-880838e4583441048050264fc4ef2504
Source dataset
uspto-grants-2016_08
Patent number
US09415026B2

Reaction notes

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