Hydrochloric Acid → (2r)-N-Hydroxy-2-Methyl-2-(Methylsulfonyl)-4-(2-Oxo-4-Phenylpyridin-1(2h)-Yl)butanamide

HRID 84239Notes

Reaction equation

HRID 84239 reaction equation
Cl.[CH3:2][C@@:3]([S:29]([CH3:32])(=[O:31])=[O:30])([CH2:14][CH2:15][N:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:18][C:17]1=[O:28])[C:4]([NH:6][O:7]C1CCCCO1)=[O:5]>O1CCOCC1.O>[OH:7][NH:6][C:4](=[O:5])[C@:3]([CH3:2])([S:29]([CH3:32])(=[O:31])=[O:30])[CH2:14][CH2:15][N:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[CH:18][C:17]1=[O:28]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57326796(2R)-2-Methyl-2-(methylsulfonyl)-4-(2-oxo-4-phenylpyridin-1(2H)-yl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

Product 1

HCID 56593152(2r)-N-Hydroxy-2-Methyl-2-(Methylsulfonyl)-4-(2-Oxo-4-Phenylpyridin-1(2h)-Yl)butanamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

HCl (4.0 N in 1,4-dioxane, 20 mL) was added to a solution of (2R)-2-Methyl-2-(methylsulfonyl)-4-(2-oxo-4-phenylpyridin-1(2H)-yl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (5.15 g, 11.5 mmol) in 1,4-dioxane (100 mL) and water (20 mL). The reaction was continued for 2 hours. The reaction was concentrated in vacuo, upon concentration a white solid precipitated. The solid was triturated with 2-propanol (150 mL) at 50° C. for 30 minutes then collected by filtration. The title compound was obtained as a white solid (3.85 g, 92%) LC-MS m/z 365.5 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.58 (s, 3 H) 2.10-2.23 (m, 1 H) 2.37-2.48 (m, 1 H) 3.11 (s, 3 H) 3.69-3.82 (m, 1 H) 4.04-4.19 (m, 1 H) 6.63-6.68 (m, 1 H) 6.70 (d, J=1.76 Hz, 1 H) 7.41-7.55 (m, 3 H) 7.68-7.75 (m, 2 H) 7.77 (d, J=6.83 Hz, 1 H) 11.17 (br. s., 1 H). [α]58920=+33.21°.

Workup

  1. concentrationThe reaction was concentrated in vacuo, upon concentration a white solid
  2. customprecipitated
  3. customThe solid was triturated with 2-propanol (150 mL) at 50° C. for 30 minutes
  4. filtrationthen collected by filtration

Sources & evidence

ORD record
ord-c9480b5d99e54a50a85da740b274d7f8
Source dataset
uspto-grants-2014_09
Patent number
US08846933B2

Reaction notes

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