Propane sultone → HCID 16036057, compound

HRID 239767Notes

Reaction equation

HRID 239767 reaction equation
[C:1]([NH:5][C:6](=[O:12])[C@H:7]([CH:9]([CH3:11])[CH3:10])[NH2:8])([CH3:4])([CH3:3])[CH3:2].[CH2:13]1[CH2:19][S:16](=[O:18])(=[O:17])[O:15][CH2:14]1>O1CCOCC1>[C:1]([NH:5][C:6]([C@@H:7]([NH:8][CH2:14][CH2:13][CH2:19][S:16]([OH:18])(=[O:17])=[O:15])[CH:9]([CH3:10])[CH3:11])=[O:12])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14264Propane sultoneHCID 7020205HCID 7020205, compound

Product 1

HCID 16036057HCID 16036057, compoundYield 30.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of L-valine tert-butylamide (1.87 g, 11.0 mmol) in 1,4-dioxane (20 mL) was added 1,3-propanesultone (1.07 g, 9.0 mmol). The solution was stirred at reflux for 5 hours. The reaction was cooled to room temperature. The solid was collected by filtration, washed with acetone (2×30 mL) and dried in vacuo, affording the title compound (801 mg, 25%). 1H NMR (D2O, 500 MHz) δ ppm 3.43 (m, 1H), 3.00 (m, 2H), 2.85 (m, 2H), 2.03 (m, 3H), 1.21 (m, 9H), 0.92 (d, 3H, J=6.3 Hz), 0.85 (d, 3H, J=6.8 Hz). 13C (D2O, 125 MHz) δ ppm 166.47, 66.55, 52.56, 48.23, 46.11, 29.91, 27.81, 21.29, 18.30, 17.44. [α]D=−11.6° (c=0.0023 in water), ES-MS 293 (M−1).

Workup

  1. temperatureat reflux for 5 hours
  2. filtrationThe solid was collected by filtration
  3. washwashed with acetone (2×30 mL)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-f4598dd3fb504c84af24d6173e3670a6
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Reaction notes

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