HCID 45086957, compound → HCID 58997949, compound

HRID 2267621Notes

Reaction equation

HRID 2267621 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C@H:11]1[C@H:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:12]1)=[O:10]>C(#N)C.[O-]S(C(F)(F)F)(=O)=O.[Sc+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>[OH:12][C@H:11]1[C:9](=[O:10])[NH:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[O:1][C@@H:13]1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 1

HCID 45086957HCID 45086957, compound

Product 1

HCID 58997949HCID 58997949, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 2734571Scandium(III) triflateCatalystHCID 6342AcetonitrileSolvent

Procedure

Scandium triflate (730 mg, 1.48 mmol) was added to a stirred suspension of (2R,3S)—N-(2-hydroxyphenyl)-3-phenyloxirane-2-carboxamide (64b) in dry acetonitrile (150 mL) under nitrogen. The mixture was stirred at ambient temperature for 24 hours then heated at reflux for an additional 1 hour. The solvent was evaporated, the residue dissolved in ethyl acetate, and filtered through diatomaceous earth. Evaporation afforded an off-white solid which was purified by flash chromatography on silica gel eluting with 10:1 (v/v) dichloromethane: ethyl acetate to afford the title compound (2.290 g, 60%) as a white solid. TLC Rf=0.20 (10:1 dichloromethane:ethyl acetate). 1H NMR (300 MHz, CDCl3) δ3.70 (d, 1H, J=5 Hz), 4.63 (m, 1H), 5.28 (d, 1H, J=10 Hz), 6.89 (m, 1H), 7.02-7.16 (m, 3H), 7.35-7.47 (m, 5H), 7.78 (br, 1H). MS APCI, m/z=256 (M+1). LC/MS: 1.84 min. [α]D 25=+288° (c=5.0, CHCl3).

Workup

  1. temperaturethen heated
  2. temperatureat reflux for an additional 1 hour
  3. customThe solvent was evaporated
  4. dissolutionthe residue dissolved in ethyl acetate
  5. filtrationfiltered through diatomaceous earth
  6. customEvaporation
  7. customafforded an off-white solid which
  8. customwas purified by flash chromatography on silica gel eluting with 10:1 (v/v) dichloromethane

Sources & evidence

ORD record
ord-4ef4e5c0b9a04d49b6b0f716cfc34132
Source dataset
uspto-grants-2010_12
Patent number
US07858776B2

Reaction notes

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