Hydrogen Bromide → HCID 66731817, compound

HRID 1963398Notes

Reaction equation

HRID 1963398 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C@H:11]2[CH2:16][C@H:15]([C:17]3[O:21][NH:20][C:19](=[O:22])[CH:18]=3)[CH2:14][CH2:13][N:12]2C(OC)=O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].Br>>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C@H:11]2[CH2:16][C@H:15]([C:17]3[O:21][NH:20][C:19](=[O:22])[CH:18]=3)[CH2:14][CH2:13][NH:12]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 131730397HCID 131730397, compound

Product 1

HCID 66731817HCID 66731817, compoundYield 47%

Procedure

Trans-methyl 2-(4-(methylsulfonyl)phenyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (301 mg, 0.79 mmol) was dissolved in hydrogen bromide (33% in acetic acid, 2 mL, 28.55 mmol) and stirred at room temperature for 20 h. The solvent was evaporated and the residue purified by preparative HPLC (Instrument: FractionLynx II, Mobilphase: gradient 5-95% MeCN in 0.2% NH3, pH 10, Column: Xbridge Prep C18 5 μm OBD 19*150 mm) to yield 5-(trans-2-(4-(methylsulfonyl)phenyl)piperidin-4-yl)isoxazol-3(2H)-one (119 mg, 47%), HRMS Calcd for [C15H18N2O4S+H]+: 323.1065. Found: 323.1054.

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified by preparative HPLC (Instrument: FractionLynx II, Mobilphase: gradient 5-95% MeCN in 0.2% NH3, pH 10, Column: Xbridge Prep C18 5 μm OBD 19*150 mm)

Sources & evidence

ORD record
ord-31e1c670ffb5404b939888d9993c00e7
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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