Propane sultone → HCID 58931883, compound

HRID 239781Notes

Reaction equation

HRID 239781 reaction equation
[CH2:1]([O:8][C:9](=[O:16])[C@H:10]([C@H:12]([CH2:14][CH3:15])[CH3:13])[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17]1[CH2:23][S:20](=[O:22])(=[O:21])[O:19][CH2:18]1>C(#N)C>[CH2:1]([O:8][C:9]([C@@H:10]([NH:11][CH2:18][CH2:17][CH2:23][S:20]([OH:22])(=[O:21])=[O:19])[CH:12]([CH3:13])[CH2:14][CH3:15])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14264Propane sultoneHCID 7350013HCID 7350013, compound

Product 1

HCID 58931883HCID 58931883, compoundYield 39.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of L-isoleucine benzylester (1.41 g, 6.4 mmol) in acetonitrile (12 mL) was added 1,3-propane sultone (706 mg, 5.8 mmol). The solution was stirred at reflux for 2 hours. The reaction mixture was cooled to room temperature. The solid was filtered and washed with acetone (2×20 mL). The solid material was dissolved in 50% EtOH/water (50 mL). Dowex Marathon C ion exchange resin (strongly acidic, 10 g) was added to the solution. The suspension was stirred for 15 minutes before the resin was removed by filtration. The filtrate was evaporated under reduced pressure and lyophilized affording the title compound (778 mg, 39%). 1H NMR (D2O, 500 MHz) δ ppm 7.49 (m, 5H), 5.42 (d, 1H, J=11.7 Hz), 5.31 (d, 1H, J=11.7 Hz), 3.24 (m, 2H), 2.98 (m, 2H), 2.13 (m, 3H), 1.46 (m, 1H), 1.34 (m, 1H), 0.93 (m, 6H). 13C (D2O, 125 MHz) δ ppm 168.53, 134.69, 129.28, 129.22, 129.06, 68.86, 64.45, 48.12, 46.56, 36.21, 25.97, 21.31, 13.73, 11.05. [α]D=−1.5° (c=0.0031 in water), ES-MS 342 (M−1).

Workup

  1. temperatureat reflux for 2 hours
  2. filtrationThe solid was filtered
  3. washwashed with acetone (2×20 mL)
  4. dissolutionThe solid material was dissolved in 50% EtOH/water (50 mL)
  5. additionDowex Marathon C ion exchange resin (strongly acidic, 10 g) 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 under reduced pressure

Sources & evidence

ORD record
ord-355a8dcc8e7940d9a5095ce179352915
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Reaction notes

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