Propane sultone → 3-{[(1r)-1-(Methoxycarbonyl)-3-methylbutyl]amino}-1-propanesulfonic acid

HRID 239778

Reaction equation

HRID 239778 reaction equation
[CH3:1][O:2][C:3](=[O:10])[C@@H:4]([CH2:6][CH:7]([CH3:9])[CH3:8])[NH2:5].[CH2:11]1[CH2:17][S:14](=[O:16])(=[O:15])[O:13][CH2:12]1>C(#N)C>[CH3:1][O:2][C:3]([C@H:4]([NH:5][CH2:12][CH2:11][CH2:17][S:14]([OH:16])(=[O:15])=[O:13])[CH2:6][CH:7]([CH3:9])[CH3:8])=[O:10]

Participants

4

Reactant 2

HCID 14264Propane sultoneHCID 89967D-Leucine, methyl ester

Product 1

HCID 160361783-{[(1r)-1-(Methoxycarbonyl)-3-methylbutyl]amino}-1-propanesulfonic acidYield 60.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of D-Leucine methylester (1.58 g, 10.9 mmol) in acetonitrile (35 mL) was added 1,3-propanesultone (1.21 g, 9.9 mmol). The solution was stirred at reflux for 2 hours. The reaction mixture was cooled to room temperature. The solid material was collected by filtration, recrystallized from EtOH and dried in vacuo, affording the title compound (1.59 g, 60%). 1H NMR (D2O, 500 MHz) δ ppm 3.98 (m, 1H), 3.70 (s, 3H), 3.11 (m, 2H), 2.85 (m, 2H), 2.00 (m, 2H), 1.72 (m, 1H), 1.60 (m, 2H), 0.81 (m, 6H). 13C (D2O, 125 MHz) δ ppm 170.51, 58.78, 53.69, 47.97, 45.36, 38.09, 24.34, 22.07, 21.51, 20.82. [α]D=+13.1° (c=0.0019 in water), ES-MS 266 (M−1).

Workup

  1. temperatureat reflux for 2 hours
  2. filtrationThe solid material was collected by filtration
  3. customrecrystallized from EtOH
  4. customdried in vacuo

Sources & evidence

ORD record
ord-8b23cc81e1fe47a4bf422cea8e94a740
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Linked notes

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