Hydrochloric Acid → (2R)-4-(4-cyano-1H-pyrazol-1-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide

HRID 2405932Notes

Reaction equation

HRID 2405932 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][N:6]([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:7]=1)#[N:2].Cl>CCO>[C:1]([C:3]1[CH:4]=[N:5][N:6]([CH2:8][CH2:9][C@@:10]([CH3:25])([S:21]([CH3:24])(=[O:22])=[O:23])[C:11]([NH:13][OH:14])=[O:12])[CH:7]=1)#[N:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86710241(2R)-4-(4-cyano-1H-pyrazol-1-yl)-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

Product 1

HCID 66558214(2R)-4-(4-cyano-1H-pyrazol-1-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamideYield 16.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (2R)-4-(4-cyano-1H-pyrazol-1-yl)-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (0.165 g, 0.445 mmol) in EtOH (20 mL) was added HCl (1 M solution, 5 mL). The reaction mixture was allowed to stir at room temperature overnight. The reaction mixture was concentrated and was purified via reverse-phase chromatography system, using 5%-95% acetonitrile/water with 0.1% formic acid modifier as the gradient elution solvent. Target fractions were combined and evaporated to yield (2R)-4-(4-cyano-1H-pyrazol-1-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide (21 mg, 16% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 1.47 (s, 3H), 2.16-2.33 (m, 1H), 2.59-2.80 (m, 1H), 3.04 (s, 3H), 3.96-4.17 (m, 1H), 4.18-4.39 (m, 1H), 8.05 (s, 1H) 8.57 (s, 1H), 9.24 (br. s., 1H) 10.97 (br. s., 1H). LC-MS M−H 285.3.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customwas purified via reverse-phase chromatography system
  3. washas the gradient elution solvent
  4. customevaporated

Sources & evidence

ORD record
ord-6aed19d6d6f5411f96ad82d3efcbda89
Source dataset
uspto-grants-2014_08
Patent number
US08809333B2

Reaction notes

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