ChemicalBook CAS DataBase List 1-Hydroxy Valdecoxib

1-Hydroxy Valdecoxib synthesis

6synthesis methods

Product Name:1-Hydroxy Valdecoxib
CAS Number:181695-81-8
Molecular formula:C16H14N2O4S
Molecular Weight:330.36

Benzenesulfonamide, 4-[5-(chloromethyl)-3-phenyl-4-isoxazolyl]-

181696-34-4
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181695-81-8
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Yield:181695-81-8 69%

Reaction Conditions:

Stage #1: 4-(5-(chloromethyl)-3-phenylisoxazol-4-yl)benzenesulfonamidewith formic acid;triethylamine in acetonitrile at 80; for 5 h;
Stage #2: with lithium hydroxide monohydrate;sodium hydroxide in acetonitrile; pH=11; for 3 h;

Steps:

S-07.D Step D.

4-(5-(chloromethyl)-3-phenylisoxazol-4-yl)benzenesulfonamide(5g, 14.3 mmol), formic acid (2.9 g, 64.3mmol) and triethylamine (3.6 g, 35.7 mmol) were heated to reflux in acetonitrile (50 mL) for 5h. The pH of the solution was adjusted to 11 with NaOH (2.5 M aq., ~20 mL) and heated to reflux for 3h then cooled to room temperature. EtOAc (100 mL) and H₂O (80 mL) were added, and the pH of the solution was adjusted to 2 by the addition of concentrated HCl. The layers were separated, and the organic layer was collected, washed with brine (100 mL), dried over Na2SO4, filtered and the filtrate was concentrated in vacuo. The residue was purified by silica gel chromatography, eluting with PE/EtOAc (60/40) to give 4-(5- (hydroxymethyl)-3-phenylisoxazol-4-yl)benzenesulfonamide (3.3 g, yield: 69 %) as a light yellow solid.¹H NMR (400 MHz, DMSO) δ 7.88 - 7.80 (m, 2H), 7.51 - 7.39 (m, 7H), 7.40 - 7.34 (m, 2H), 5.78 (t, J = 5.8 Hz, 1H), 4.56 (d, J = 5.5 Hz, 2H). Mass Spectrum (ESI) m/z = 331 (M+1).

References:

WO2022/76741,2022,A1 Location in patent:Paragraph 0190

181695-72-7 Synthesis