Propane sultone → HCID 16035946, compound

HRID 239759Notes

Reaction equation

HRID 239759 reaction equation
[CH3:1][O:2][C:3](=[O:9])[C@H:4]([CH:6]([CH3:8])[CH3:7])[NH2:5].[CH2:10]1[CH2:16][S:13](=[O:15])(=[O:14])[O:12][CH2:11]1>C1COCC1>[CH3:1][O:2][C:3]([C@@H:4]([NH:5][CH2:11][CH2:10][CH2:16][S:13]([OH:15])(=[O:14])=[O:12])[CH:6]([CH3:8])[CH3:7])=[O:9]

Participants

4

Reactant 2

HCID 14264Propane sultoneHCID 94285Valine methyl ester

Product 1

HCID 16035946HCID 16035946, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of L-valine methylester in THF (25 mL) was slowly added 1,3-propanesultone (2.49 g, 19.9 mmol). The solution was stirred at reflux for 2 hours. The reaction was cooled to room temperature. The solid was collected by filtration, washed with acetone (2×30 mL). It was dried in the vacuum oven (50° C.) affording the title compound (2.52 g, 50%). 1H NMR (D2O, 500 MHz) δ ppm 3.92 (m, 1H), 3.75 (s, 3H), 3.13 (t, 2H, J=6.8 Hz), 2.88 (t, 2H, J=6.8 Hz), 2.24 (m, 1H), 2.06 (m, 2H)), 0.96 (d, 3H, J=6.8 Hz), 0.88 (d, 3H, J=6.8 Hz). 13C (D2O, 125 MHz) δ ppm 169.35, 65.85, 55.61, 48.14, 45.59, 29.48, 21.32, 18.25, 16.57. [α]D=+9.6° (c=0.0014 in water), ES-MS 254 (M+1).

Workup

  1. temperatureat reflux for 2 hours
  2. filtrationThe solid was collected by filtration
  3. washwashed with acetone (2×30 mL)
  4. customIt was dried in the vacuum oven (50° C.)

Sources & evidence

ORD record
ord-1207b74bf3e04ebd8219931aaa41fb2f
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Reaction notes

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