Hydrogen Bromide → HCID 66732200, compound

HRID 1963593Notes

Reaction equation

HRID 1963593 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 66735002HCID 66735002, compound

Product 1

HCID 66732200HCID 66732200, compoundYield 47.5%

Procedure

(2S,4R)-Methyl 2-(4-(methylsulfonyl)benzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (225 mg, 0.57 mmol) was dissolved in HBr (33% in acetic acid, 5 mL, 28.55 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-((2S,4R)-2-(4-(methylsulfonyl)benzyl)piperidin-4-yl)isoxazol-3(2H)-one (91 mg, 47.4%). 1H NMR (600 MHz, dmso) δ 1.05-1.14 (m, 1H), 1.30-1.38 (m, 1H), 1.72-1.79 (m, 2H), 2.39-2.56 (omitted signals), 2.62-2.80 (m, 4H), 2.94-3.00 (m, 1H), 3.16 (s, 3H), 5.68 (s, 1H), 7.46 (d, 2H), 7.80 (d, 2H). HRMS Calcd for [C16H20N2O4S+H]+: 337.1222. Found: 337.1198

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-48fe2d9e6c89420e9bdacc84d8fcfa96
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

Loading…