Trifluoroacetic acid → HCID 178516059, compound

HRID 1689780Notes

Reaction equation

HRID 1689780 reaction equation
[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:10]=3[Cl:16])[C:5]=2[CH2:17][O:18][C@H:19]2[CH2:24][CH2:23][C@H:22]([C:25]3[CH:30]=[CH:29][C:28]([O:31]CC4C=CC(OC)=CC=4)=[CH:27][CH:26]=3)[CH2:21][CH2:20]2)[CH2:3][CH2:2]1.COC1C=CC=CC=1.FC(F)(F)C(O)=O>ClCCl>[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[C:10]([Cl:16])=[CH:11][CH:12]=[CH:13][C:14]=3[Cl:15])[C:5]=2[CH2:17][O:18][C@H:19]2[CH2:20][CH2:21][C@H:22]([C:25]3[CH:26]=[CH:27][C:28]([OH:31])=[CH:29][CH:30]=3)[CH2:23][CH2:24]2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 178491286HCID 178491286, compound

Product 1

HCID 178516059HCID 178516059, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trans-5-cyclopropyl-3-(2,6-dichloro-phenyl)-4-{4-[4-(4-methoxy-benzyloxy)-phenyl]-cyclohexyloxymethyl}isoxazole (1.33 mmol, 770.00 mg) in dichloromethane (17 mL) is treated at room temperature with methoxybenzene (13.3 mmol, 1.45 mL) and trifluoroacetic acid (8.5 mL). The solution is stirred for 2 h and concentrated under reduced pressure. The residue is co-evaporated with CCl4 (2×) and triturated with hexanes. The crude product is supported on silica gel and purified by flash chromatography (120 g silica) eluting with a gradient of 20-50% EtOAc in hexane to give the title compound (544 mg, 89%) as a white solid. MS m/z 458.0 (M+1).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customtriturated with hexanes
  3. custompurified by flash chromatography (120 g silica)
  4. washeluting with a gradient of 20-50% EtOAc in hexane

Sources & evidence

ORD record
ord-f4328a7704e642298ca2feede8067d1c
Source dataset
uspto-grants-2012_04
Patent number
US08153624B2

Reaction notes

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