Tetrahydrofuran → HCID 87095505, compound

HRID 239775Notes

Reaction equation

HRID 239775 reaction equation
C(O[C:5](=[O:11])[C@H:6]([CH:8]([CH3:10])[CH3:9])[NH2:7])C=C.[CH2:12]1[CH2:18][S:15](=[O:17])(=[O:16])[O:14][CH2:13]1.O1C[CH2:22][CH2:21][CH2:20]1>O1CCOCC1.CO>[CH:8]([C@H:6]([NH:7][CH2:13][CH2:12][CH2:18][S:15]([OH:14])(=[O:17])=[O:16])[C:5](=[O:11])[CH2:22][CH:21]=[CH2:20])([CH3:9])[CH3:10]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 14264Propane sultoneHCID 7018865HCID 7018865, compound

Product 1

HCID 87095505HCID 87095505, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of L-valine allylester (1.30 g, 8.3 mmol) in tetrahydrofuran (6 mL), 1,4-dioxane (6 mL) and MeOH (0.5 mL) was added 1,3-propanesultone (910 mg, 7.5 mmol). The solution was stirred at reflux for 2 hours. The reaction was cooled to room temperature. The solvent was evaporated under reduced pressure. The sticky paste was suspended in 20% acetone/ether. The solid was filtered and dissolved EtOH (75 mL). Dowex Marathon C ion exchange resin (strongly acidic) was added to the solution. The suspension was stirred for 15 minutes before the resin was removed by filtration. The filtrate was evaporated to dryness under reduced pressure, affording the title compound (605 mg, 26%). 1H NMR (D2O, 500 MHz) δ ppm 5.84 (m, 1H), 5.27 (d, 1H, J=17.1 Hz), 5.19 (m, 1H, J=10.3 Hz), 3.91 (d, 1H, J=3.9 Hz), 3.10 (t, 2H, J=7.3 Hz), 2.85 (t, 2H, J=7.3 Hz), 2.22 (m, 1H), 2.03 (m, 2H), 0.93 (d, 3H, J=6.8 Hz), 0.85 (d, 3H, J=6.8 Hz). 13C (D2O, 125 MHz) δ ppm 168.55, 130.90, 120.31, 67.58, 65.82, 48.09, 46.57, 29.53, 21.29, 18.25, 16.57. [α]D=+5.0° (c=0.0011 in water), ES-MS 278 (M−1).

Workup

  1. temperatureat reflux for 2 hours
  2. customThe solvent was evaporated under reduced pressure
  3. filtrationThe solid was filtered
  4. dissolutiondissolved EtOH (75 mL)
  5. additionDowex Marathon C ion exchange resin (strongly acidic) was added to the solution
  6. stirringThe suspension was stirred for 15 minutes before the resin
  7. customwas removed by filtration
  8. customThe filtrate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-c01ca85874574426bab6de6cc9a193c0
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Reaction notes

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