Trifluoroacetic acid → HCID 59321585, compound

HRID 2423447Notes

Reaction equation

HRID 2423447 reaction equation
CC([O:5][CH2:6][C:7]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([CH:16]([CH3:18])[CH3:17])[O:9][N:8]=1)(C)C.FC(F)(F)C(O)=O>ClCCl>[OH:5][CH2:6][C:7]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([CH:16]([CH3:18])[CH3:17])[O:9][N:8]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59709034Methyl 3-{[(1,1-dimethylethyl)oxy]methyl}-5-(1-methylethyl)-4-isoxazolecarboxylate

Product 1

HCID 59321585HCID 59321585, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 3-{[(1,1-dimethylethyl)oxy]methyl}-5-(1-methylethyl)-4-isoxazolecarboxylate (500 mg, 1.96 mmol) in dichloromethane (97 mL) was added trifluoroacetic acid (97 mL, 1.25 mol). The solution was stirred at ambient temperature for approximately 45 minutes and then concentrated. The residue was taken up with ethyl acetate and poured into saturated sodium bicarbonate. Solid sodium bicarbonate followed by solid sodium carbonate were added until the pH was basic. The aqueous layer was extracted with ethyl acetate and the combined organic layers were dried over magnesium sulfate, concentrated and purified by chromatography (silica gel, 25% ethyl acetate in hexanes) to afford the methyl 3-(hydroxymethyl)-5-(1-methylethyl)-4-isoxazolecarboxylate (304 mg, 78%). 1H-NMR (400 MHz, DMSO-d6) δ 5.29 (t, J=6 Hz, 1H), 4.62 (d, J=6 Hz, 2H), 3.77 (s, 3H), 3.68 (septet, J=7 Hz, 1H), 1.25 (d, J=7 Hz, 6H).

Workup

  1. concentrationconcentrated
  2. additionpoured into saturated sodium bicarbonate
  3. additionwere added until the pH
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. dry with materialthe combined organic layers were dried over magnesium sulfate
  6. concentrationconcentrated
  7. custompurified by chromatography (silica gel, 25% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-88e484a477d64cbf96e9c5cfc5e839f9
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

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