Potassium Carbonate → HCID 52938487, compound

HRID 1482465Notes

Reaction equation

HRID 1482465 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(=O)([O-])[O-].[K+].[K+].[N:29]1([C:35](Cl)=[O:36])[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1>C1COCC1>[N:29]1([C:35]([NH:19][C@@H:15]([CH2:14][S:13][CH2:12]/[CH:11]=[C:10](\[CH3:20])/[CH2:9][CH2:8]/[CH:7]=[C:6](\[CH3:21])/[CH2:5][CH2:4][CH:3]=[C:2]([CH3:22])[CH3:1])[C:16]([OH:18])=[O:17])=[O:36])[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 848104-Morpholinecarbonyl chlorideHCID 6438372Farnesylcysteine

Product 1

HCID 52938487HCID 52938487, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 100 mL round bottom flask, S-trans, trans-farnesyl-L-cysteine (325 mg, 1.0 mmole) and potassium carbonate (1.3 g, 10 mmole) were dissolved in THF (50 mL). 4-morpholine carbonyl chloride (160 mg, 1.2 mmole) was added. The reaction mixture was stirred at room temperature for 47 hours. THF was removed by rotary evaporation. The crude material was washed with water (10 mL) and 1N HCl solution (10 mL). The remaining crude material was purified by preparative HPLC (120 mg, 27% yield) to yield Compound H: 1H-NMR (500 MHz, CDCl3) δ 1.60 (bs, 6H), 1.66 (s, 3H), 1.67 (s, 3H), 1.95-2.12 (m, 8H), 2.94-3.02 (m, 2H), 3.10-3.20 (m, 2H), 3.40-3.44 (m, 4H), 3.71 (t, J=4.8 Hz, 4H), 4.55 (dd, J=6.3, 11.6 Hz, 1H), 5.09 (t, J=6.9 Hz, 2H), 5.19 (t, J=7.6 Hz, 1H). 13C-NMR (125 MHz, CDCl3): δ 16.0, 16.2, 17.7, 25.7, 26.4, 26.7, 29.9, 33.0, 39.6, 39.7, 44.0, 53.0, 66.3, 119.4, 123.7, 124.3, 131.3, 135.4, 140.2, 157.7, 174.1; ES-MS: mass calcd for Chemical Formula: C23H38N2O4S 438.3 (M+). Found (M+Na) m/z 461.4.

Workup

  1. customTHF was removed by rotary evaporation
  2. washThe crude material was washed with water (10 mL) and 1N HCl solution (10 mL)
  3. customThe remaining crude material was purified by preparative HPLC (120 mg, 27% yield)

Sources & evidence

ORD record
ord-fee13480d81b4ffbb13186366a641bca
Source dataset
uspto-grants-2016_08
Patent number
US09415026B2

Reaction notes

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