1,2-Epoxybutane → HCID 69882854, compound

HRID 2120362Notes

Reaction equation

HRID 2120362 reaction equation
C[O-].[Na+].[Cl:4][C:5]1[C:10]([Cl:11])=[C:9]([SH:12])[CH:8]=[CH:7][C:6]=1[NH:13][C:14](=[O:22])[C@:15]([OH:21])([CH3:20])[C:16]([F:19])([F:18])[F:17].[O:23]1[CH:25]([CH2:26][CH3:27])[CH2:24]1.CCOC(C)=O>C1COCC1>[OH:23][CH:25]([CH2:26][CH3:27])[CH2:24][S:12][C:9]1[CH:8]=[CH:7][C:6]([NH:13][C:14](=[O:22])[C@:15]([OH:21])([CH3:20])[C:16]([F:17])([F:18])[F:19])=[C:5]([Cl:4])[C:10]=1[Cl:11]

Participants

6

Reactant 4

HCID 78341,2-EpoxybutaneHCID 8857Ethyl AcetateHCID 10942334Sodium MethoxideHCID 69825004HCID 69825004, compound

Product 1

HCID 69882854HCID 69882854, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium methoxide (0.075 g) was added to a stirred solution of (R)-N-[2,3-dichloro-4-mercaptophenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Method 35) (0.44 g) in anhydrous THF (10 ml). The reaction mixture was stirred at ambient temperature for 5 minutes and 1,2-epoxybutane (0.11 ml) was added. The mixture was heated under reflux for 2 hours and allowed to cool to ambient temperature. EtOAc (150 ml) was added and the mixture washed with brine (100 ml) and dried. Volatile material was removed by evaporation and the residue was purified on a 20 g silica Mega Bond Elut column eluting with 1-40% EtOAc/isohexane to give the title compound (0.259 g) as an orange solid. NMR: 0.88 (t, 3H), 1.35-1.49 (m, 1H), 1.58 (s, 3H), 2.97-3.08 (m, 1H), 3.53-3.62 (m, 1H), 5.00 (d, 1H), 7.42 (d, 1H), 7.77 (d, 1H), 9.79 (brs, 1H); m/z: 404.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperatureto cool to ambient temperature
  4. washthe mixture washed with brine (100 ml)
  5. customdried
  6. customVolatile material was removed by evaporation
  7. customthe residue was purified on a 20 g silica Mega Bond Elut column
  8. washeluting with 1-40% EtOAc/isohexane

Sources & evidence

ORD record
ord-12563003f60f4101b9293662bd6da3e2
Source dataset
uspto-grants-2004_02
Patent number
US06689909B1

Reaction notes

Loading…