Hydrochloric Acid → (2R)-N-hydroxy-2-methyl-2-(methylsulfonyl)-4-{2-oxo-4-[(E)-2-phenylvinyl]pyridin-1(2H)-yl}butanamide

HRID 84218Notes

Reaction equation

HRID 84218 reaction equation
Cl.[CH3:2][C@@:3]([S:31]([CH3:34])(=[O:33])=[O:32])([CH2:14][CH2:15][N:16]1[CH:21]=[CH:20][C:19](/[CH:22]=[CH:23]/[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:18][C:17]1=[O:30])[C:4]([NH:6][O:7]C1CCCCO1)=[O:5]>ClCCl.CO>[OH:7][NH:6][C:4](=[O:5])[C@:3]([CH3:2])([S:31]([CH3:34])(=[O:33])=[O:32])[CH2:14][CH2:15][N:16]1[CH:21]=[CH:20][C:19](/[CH:22]=[CH:23]/[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[CH:18][C:17]1=[O:30]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86671909(2R)-2-methyl-2-(methylsulfonyl)-4-{2-oxo-4-[(E)-2-phenylvinyl]pyridin-1(2H)-yl}-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

Product 1

HCID 57326986(2R)-N-hydroxy-2-methyl-2-(methylsulfonyl)-4-{2-oxo-4-[(E)-2-phenylvinyl]pyridin-1(2H)-yl}butanamideYield 100.6%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of hydrochloric acid (2.5 mL, 4.0 M in 1,4-dioxane) was added to a solution of (2R)-2-methyl-2-(methylsulfonyl)-4-{2-oxo-4-[(E)-2-phenylvinyl]pyridin-1(2H)-yl}-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (40 mg, 0.084 mmol) in 5:1 dichloromethane-methanol (2.5 mL) at 0° C. After 4 h, the reaction was concentrated under reduced pressure. The resulting residue was triturated with 1:1 pentane-diethyl ether, filtered, washed with pentane and dried under reduced pressure to provide a light yellow solid (33 mg, 76%). MS (LCMS) m/z 391.4 (M+1). 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.69 (s, 3 H) 2.30-2.42 (m, 1 H) 2.56-2.69 (m, 1 H) 3.08 (s, 3 H) 3.93-4.06 (m, 1 H) 4.32 (td, J=11.76, 4.98 Hz, 1 H) 6.75 (s, 1 H) 7.00 (d, J=6.24 Hz, 1 H) 7.11 (d, J=16.39 Hz, 1 H) 7.30-7.42 (m, 3 H) 7.47 (d, J=16.39 Hz, 1 H) 7.62 (d, J=7.02 Hz, 2 H) 7.75 (s, 1 H)

Workup

  1. concentrationthe reaction was concentrated under reduced pressure
  2. customThe resulting residue was triturated with 1:1 pentane-diethyl ether
  3. filtrationfiltered
  4. washwashed with pentane
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-f0335a7b87ce4fef8803592c8b0ee25f
Source dataset
uspto-grants-2014_09
Patent number
US08846933B2

Reaction notes

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