Hydrogen Bromide → HCID 66732445, compound

HRID 1963594Notes

Reaction equation

HRID 1963594 reaction equation
[CH3:1][S:2]([C:5]1[CH:27]=[CH:26][C:8]([CH2:9][C@H:10]2[CH2:15][C@H:14]([C:16]3[O:20][NH:19][C:18](=[O:21])[CH:17]=3)[CH2:13][CH2:12][N:11]2C(OC)=O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].Br>>[CH3:1][S:2]([C:5]1[CH:27]=[CH:26][C:8]([CH2:9][C@H:10]2[CH2:15][C@H:14]([C:16]3[O:20][NH:19][C:18](=[O:21])[CH:17]=3)[CH2:13][CH2:12][NH:11]2)=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 131730479HCID 131730479, compound

Product 1

HCID 66732445HCID 66732445, compoundYield 102%

Procedure

Trans-methyl 2-(4-(methylsulfonyl)benzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (185 mg, 0.47 mmol) was dissolved in HBr (33% in acetic acid, 4 mL, 22.84 mmol) and the mixture was stirred at room temperature overnight. 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)benzyl)piperidin-4-yl)isoxazol-3(2H)-one (161 mg, 102%). 1H NMR (600 MHz, dmso) δ 1.65-1.97 (m, 4H), 2.34-2.63 (omitted signals), 2.80-3.15 (m, 5H), 3.18 (s, 3H), 5.84 (s, 1H), 7.51 (d, 2H), 7.87 (d, 2H). HRMS Calcd for [C16H20N2O4S+H]+: 337.1222. Found: 337.1236

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-a5d947d687b24d46bd51a815f2147caf
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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