Propane sultone → 3-[(1S)-1-carbamoyl-2-methylpropyl]amino-1-propanesulfonic acid

HRID 239752Notes

Reaction equation

HRID 239752 reaction equation
[NH2:1][C@H:2]([C:6]([NH2:8])=[O:7])[CH:3]([CH3:5])[CH3:4].[CH2:9]1[CH2:15][S:12](=[O:14])(=[O:13])[O:11][CH2:10]1>O1CCCC1.O>[C:6]([C@@H:2]([NH:1][CH2:10][CH2:9][CH2:15][S:12]([OH:14])(=[O:13])=[O:11])[CH:3]([CH3:5])[CH3:4])(=[O:7])[NH2:8]

Participants

5

Reactant 2

HCID 14264Propane sultoneHCID 445637Valinamide

Product 1

HCID 160358423-[(1S)-1-carbamoyl-2-methylpropyl]amino-1-propanesulfonic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of L-valinamide (1.57 g, 13.5 mmol) in tetrahydrofuran (20 mL) was slowly added 1,3-propane sultone (1.61 g, 12.9 mmol). The mixture was stirred at reflux for 2 hours. The reaction mixture was cooled to room temperature. The solid material was collected by filtration, washed with acetone (2×25 mL). The crude product was dissolved in water (60 mL) and treated with ion exchange resin Dowex Marathon C (strongly acidic, 15 g). The mixture was stirred for 15 minutes. The resin was removed by filtration. The filtrate was poured into EtOH (250 mL). The solid product, after the completion of the precipitation, was collected by filtration, and dried in vacuo, to afford compound EQ (1.6 g, 51%). 1H NMR (D2O, 500 MHz) δ ppm 3.63 (d, 1H), 3.05 (m, 2H), 2.85 (m, 2H), 2.05 (m, 4H), 0.93 (d, 3H), 0.88 (d, 3H). 13C NMR (D2O, 125 MHz) δ ppm 170.24, 65.92, 48.16, 46.31, 29.59, 21.31, 18.02, 17.07. [α]D=+10.5° (c=0.0027 in water), ES-MS 237 (M−1).

Workup

  1. temperatureat reflux for 2 hours
  2. filtrationThe solid material was collected by filtration
  3. washwashed with acetone (2×25 mL)
  4. dissolutionThe crude product was dissolved in water (60 mL)
  5. additiontreated with ion exchange resin Dowex Marathon C (strongly acidic, 15 g)
  6. stirringThe mixture was stirred for 15 minutes
  7. customThe resin was removed by filtration
  8. additionThe filtrate was poured into EtOH (250 mL)
  9. customThe solid product, after the completion of the precipitation
  10. filtrationwas collected by filtration
  11. customdried in vacuo
  12. customto afford compound EQ (1.6 g, 51%)

Sources & evidence

ORD record
ord-b1a263d1898344c590f940a3368082d5
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Reaction notes

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