Hydrochloric Acid → (+/-)-N-Hydroxy-2-methyl-2-(methylsulfonyl)-4-(4'-nitrobiphenyl-4-yl)butanamide

HRID 533536Notes

Reaction equation

HRID 533536 reaction equation
Cl.[CH3:2][C:3]([S:31]([CH3:34])(=[O:33])=[O:32])([CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=2)=[CH:18][CH:17]=1)[C:4]([NH:6][O:7]C1CCCCO1)=[O:5]>O1CCOCC1.C(Cl)Cl>[OH:7][NH:6][C:4](=[O:5])[C:3]([CH3:2])([S:31]([CH3:34])(=[O:33])=[O:32])[CH2:14][CH2:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=2)=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86668765(+/-)-2-Methyl-2-(methylsulfonyl)-4-(4'-nitrobiphenyl-4-yl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

Product 1

HCID 51049986(+/-)-N-Hydroxy-2-methyl-2-(methylsulfonyl)-4-(4'-nitrobiphenyl-4-yl)butanamideYield 87%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of HCl in dioxane (4.0 M, 10 mL) was added to a solution of (+/−)-2-methyl-2-(methylsulfonyl)-4-(4′-nitrobiphenyl-4-yl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (700 mg, 1.47 mmol) in DCM (5 mL) at 0° C. The reaction was warmed to room temperature as the ice bath expired. After 4 hours the reaction was concentrated. Purification on silica by flash column chromatography (DCM/MeOH 99:1-95:5) afforded the title compound as a yellow solid (500 mg, 87%). LCMS m/z 391.1 (M−1). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.57 (s, 3H) 1.87-2.01 (m, 1H) 2.35-2.59 (m, 2H) 2.64-2.80 (m, 1H) 3.05 (s, 3H) 7.41 (d, J=8.20 Hz, 2H) 7.74 (d, J=8.59 Hz, 2H) 7.88-8.06 (m, 2H) 8.22-8.39 (m, 2H) 9.23 (br. s., 1H) 10.98 (s, 1H)

Workup

  1. concentrationAfter 4 hours the reaction was concentrated
  2. customPurification on silica by flash column chromatography (DCM/MeOH 99:1-95:5)

Sources & evidence

ORD record
ord-7b0259eb61f04f1dbc8b4a2d798f604c
Source dataset
uspto-grants-2014_10
Patent number
US08853258B2

Reaction notes

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