Propane sultone → HCID 58931811, compound

HRID 239762Notes

Reaction equation

HRID 239762 reaction equation
[CH:1]1([NH:7][C:8](=[O:18])[C@H:9]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[NH2:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:19]1[CH2:25][S:22](=[O:24])(=[O:23])[O:21][CH2:20]1>O1CCCC1>[CH2:11]([C@H:9]([NH:10][CH2:20][CH2:19][CH2:25][S:22]([OH:24])(=[O:23])=[O:21])[C:8]([NH:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:18])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 14264Propane sultoneHCID 688648L-Phenylalanine-cyclohexylamide

Product 1

HCID 58931811HCID 58931811, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of L-Phenylalanine cyclohexylamide (2.5 g, 10.1 mmol) in tetrahydrofuran (25 mL) was added 1,3-propanesultone (1.17 g, 9.7 mmol). The solution was stirred at reflux for 2 hours. It was cooled to room temperature. The solid was collected by filtration, washed with acetone (2×25 mL) and dried in the vacuum oven (50° C.), affording the title compound (1.39 g, 39%). 1H NMR (D2O, 500 MHz) δ ppm 7.21 (m, 3H), 7.08 (m, 2H), 4.42 (m, 0.5H), 3.83 (m, 1H). 3.29 (m, 1H), 3.15 (m, 1H), 3.02 (m, 2H), 2.86 (m, 3H), 2.49 (m, 0.5H), 2.01 (m, 2H), 1.54 (m, 1H), 1.45 (m, 1H), 1.33 (m, 2H), 1.02 (m, 4H), 0.55 (m, 1H). 13C (D2O, 125 MHz) δ ppm 133.71, 129.54, 129.18, 128.03, 62.08, 49.25, 47.97, 45.41, 36.29, 31.73, 31.46, 24.86, 24.28, 24.20, 21.39. [α]D=+36.4° (c=0.0019 in water), ES-MS 369 (M+1).

Workup

  1. temperatureat reflux for 2 hours
  2. filtrationThe solid was collected by filtration
  3. washwashed with acetone (2×25 mL)
  4. customdried in the vacuum oven (50° C.)

Sources & evidence

ORD record
ord-0d46f31f4b5e489ca52aea2a22bccbf2
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Reaction notes

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