1-Hydroxy Valdecoxib synthesis
- 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]-](/CAS/20210305/GIF/181696-34-4.gif)
181696-34-4
0 suppliers
inquiry
181695-81-8
15 suppliers
$1320.00/100mg
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
353 suppliers
$5.00/100mg
181695-81-8
15 suppliers
$1320.00/100mg
451-40-1
385 suppliers
$13.43/1gm:
181695-81-8
15 suppliers
$1320.00/100mg
952-06-7
108 suppliers
$67.00/500mg
181695-81-8
15 suppliers
$1320.00/100mg
181696-73-1
113 suppliers
$120.50/50mg
181695-81-8
15 suppliers
$1320.00/100mg