Hydrochloric Acid → (2R)-4-Biphenyl-4-yl-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide

HRID 533542Notes

Reaction equation

HRID 533542 reaction equation
Cl.[C:2]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C@@:10]([CH3:25])([S:21]([CH3:24])(=[O:23])=[O:22])[C:11]([NH:13][O:14]C2CCCCO2)=[O:12])=[CH:4][CH:3]=1>CO>[C:2]1([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C@@:10]([CH3:25])([S:21]([CH3:24])(=[O:23])=[O:22])[C:11]([NH:13][OH:14])=[O:12])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86668767(2R)-4-Biphenyl-4-yl-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

Product 1

HCID 51355576(2R)-4-Biphenyl-4-yl-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamideYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of hydrochloric acid (4.2 mL, 4.0 M in 1,4-dioxane) was added to (2R)-4-biphenyl-4-yl-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (72 mg, 0.17 mmol). The reaction was allowed to stir at room temperature for 15 min, then anhydrous methanol (10 mL) was added. After 1 h, the reaction was concentrated under reduced pressure to provide a residue that was triturated with diethyl ether (35 mL). The ether was decanted off and the residual solvent was removed under reduced pressure to provide the title compound as an off-white solid (32 mg, 55%). LCMS m/z 348.2 (M+1). 1H NMR (400 MHz, CDCl3) δ 1.62 (s, 3H), 2.09 (m, 1H), 2.45-2.56 (m, 2H), 2.65 (m, 1H), 2.96 (s, 3H), 7.21 (d, J=8.3 Hz, 2H), 7.25-7.29 (m, 1H), 7.34-7.39 (m, 2H), 7.46 (d, J=8.3 Hz, 2H), 7.49-7.52 (m, 2H).

Workup

  1. waitAfter 1 h
  2. concentrationthe reaction was concentrated under reduced pressure
  3. customto provide a residue that
  4. customwas triturated with diethyl ether (35 mL)
  5. customThe ether was decanted off
  6. customthe residual solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-178c3e78410a47828b419d63b8b1e135
Source dataset
uspto-grants-2014_10
Patent number
US08853258B2

Reaction notes

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