Lawesson's reagent → HCID 9926976, compound

HRID 1108557Notes

Reaction equation

HRID 1108557 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:13]2[CH2:17][CH:16]([CH2:18][NH:19][C:20](=O)[CH3:21])[O:15][N:14]=2)[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[CH:11][CH:10]=[CH:9]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:32])=CC=1>O1CCOCC1>[F:1][C:2]1[CH:3]=[C:4]([C:13]2[CH2:17][CH:16]([CH2:18][NH:19][C:20](=[S:32])[CH3:21])[O:15][N:14]=2)[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[CH:11][CH:10]=[CH:9]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 9904454HCID 9904454, compound

Product 1

HCID 9926976HCID 9926976, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(-)-5-Acetamidomethyl-3-(3-fluoro-4-(pyrrol-1-yl)phenyll)isoxazoline (Example 12) (452 mg) is combined with Lawesson's Reagent (655 mg) in 5 ml dioxane in a 25 ml one neck round bottom flask under nitrogen. The reaction is warmed to reflux for 30 minutes and is cooled to room temperature. The insoluble material is removed by filtration and the filtrate is concentrated in vacuo to an amber syrup. The crude material is chromatographed two times over 25 g silica gel (230-400 mesh), eluting with 3% methanol/dichloromethane while collecting 5 ml fractions. Fractions 10-30 are combined and concentrated to provide 345 mg of the title compound as an off-white solid, mp 152-153° C., [α]25D -27 (c 0.60, ethanol).

Workup

  1. temperatureThe reaction is warmed
  2. temperatureto reflux for 30 minutes
  3. customThe insoluble material is removed by filtration
  4. concentrationthe filtrate is concentrated in vacuo to an amber syrup
  5. customThe crude material is chromatographed two times over 25 g silica gel (230-400 mesh)
  6. washeluting with 3% methanol/dichloromethane
  7. customwhile collecting 5 ml fractions
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6b13db3a9afd4c3c997c7541f5b6ced2
Source dataset
uspto-grants-2000_05
Patent number
US06069141

Reaction notes

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