Lithium Hydroxide → HCID 46209176, compound

HRID 388168Notes

Reaction equation

HRID 388168 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.[Li+].[OH-:33].[C:34]([O:37]CC)(=[O:36])[CH3:35]>C(Cl)Cl.C1COCC1.O>[C:34]([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:33])([OH:37])=[O:36]

Participants

8

Reactant 4

HCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 6438372Farnesylcysteine

Product 1

HCID 46209176HCID 46209176, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a 100 mL round bottom flask, 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 chloro oxoacetate (122 mg, 1 mmol) was added to the reaction mixture. The reaction solution was stirred at room temperature overnight. Reaction solvent was removed by rotary evaporation. The remained residue was dissolved in ethyl acetate (100 mL) and washed with an NH4Cl saturated solution (50 mL), dried over Na2SO4 and concentrated to afford a crude mixture. The crude reaction mixture and LiOH (126 mg, 3 mmol) were mixed in THF (3 mL) and water (3 mL). The reaction solution was stirred at room temperature for 4 hours. Ethyl acetate (50 mL) was added and then washed with 1N HCl (20 mL×2) and brine (20 mL×2) sequentially. The ethyl acetate solution was dried by Na2SO4 and concentrated in vacuo to afford a crude mixture. The crude mixture was purified by HPLC (60 mg, 16%) to yield Compound N-19. 1H-NMR (500 MHz, CD3OD): δ 1.60 (bs, 6H), 1.68 (s, 3H), 1.73 (s, 3H), 1.99 (t, J=7 Hz, 2H), 2.02-2.15 (m, 6H), 2.88 (dd, J=8.5, 14.0 Hz, 1H), 3.08 (dd, J=4.0, 14.0 Hz, 1H), 3.15 (dd, J=5.5, 13.5 Hz, 1H), 3.28 (dd, J=5.5, 13.0 Hz, 1H), 4.64 (dd, J=4.0, 7.5 Hz, 1H), 5.09-5.13 (m, 2H), 5.19 (t, J=7.5 Hz, 1H). 13C-NMR (125 MHz, CD3OD): δ 16.1, 16.2, 26.0, 27.4, 27.8, 30.2, 33.0, 40.8, 40.9, 53.7, 121.5, 125.1, 125.5, 132.1, 136.3, 140.7, 160.3, 162.4, 173.0; ES-MS: mass calcd for Chemical Formula: C20H31NO5S 397.5. Found (M+Na) m/z 420.2.

Workup

  1. customReaction solvent
  2. customwas removed by rotary evaporation
  3. dissolutionThe remained residue was dissolved in ethyl acetate (100 mL)
  4. washwashed with an NH4Cl saturated solution (50 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto afford a crude mixture
  8. stirringThe reaction solution was stirred at room temperature for 4 hours
  9. washwashed with 1N HCl (20 mL×2) and brine (20 mL×2) sequentially
  10. dry with materialThe ethyl acetate solution was dried by Na2SO4
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e5233841f36445628d24b78c959215e5
Source dataset
uspto-grants-2013_02
Patent number
US08372884B2

Reaction notes

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