Propane sultone → HCID 16036181, compound

HRID 239786Notes

Reaction equation

HRID 239786 reaction equation
[CH2:1]([O:8][C:9](=[O:16])[C@@H:10]([CH2:12][CH:13]([CH3:15])[CH3:14])[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.CO>[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])[CH2:12][CH:13]([CH3:14])[CH3:15])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14264Propane sultoneHCID 6942172HCID 6942172, compound

Product 1

HCID 16036181HCID 16036181, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of D-Leucine benzylester (6.3 mmol) in acetonitrile (9 mL) and MeOH (3 mL) was added 1,3-propane sultone (691 mg, 5.7 mmol). The solution was stirred at reflux for 2.5 hours. The reaction mixture was cooled to room temperature. The solid material was filtered and washed with aconitrile (2×20 mL). The solid was dissolved in 20% water/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 under reduced pressure and dried in vacuo, affording the title compound (960 mg, 49%). 1H NMR (D2O, 500 MHz) δ ppm 7.52 (m, 5H), 5.41 (d, 1H, J=12.2 Hz), 5.35 (d, 1H, J=12.2 Hz), 4.16 (m, 1H), 3.22 (m, 2H), 2.97 (t, 2H, J=6.8 Hz), 2.16 (m, 2H), 1.88 (m, 1H), 1.79 (m, 1H), 1.76 (m, 1H), 0.94 (d, 6H, J=3.9 Hz). 13C (DMSO, 125 MHz) δ ppm 169.60, 135.62, 129.24, 129.21, 129.11, 68.08, 58.09, 49.87, 46.48, 24.77, 23.50, 22.50, 22.04. [α]D=−2.1° (c=0.00095 in water), ES-MS 344 (M+1).

Workup

  1. temperatureat reflux for 2.5 hours
  2. filtrationThe solid material was filtered
  3. washwashed with aconitrile (2×20 mL)
  4. dissolutionThe solid was dissolved in 20% water/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 under reduced pressure
  9. customdried in vacuo

Sources & evidence

ORD record
ord-c57474c7788d4de3a2ec9f8a41fb4e7b
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Reaction notes

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