Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → (2R)-N-hydroxy-2-methyl-4-(3-methyl-4-phenyl-1H-pyrazol-1-yl)-2-(methylsulfonyl)butanamide

HRID 2405922Notes

Reaction equation

HRID 2405922 reaction equation
[CH3:1][C@@:2]([S:27]([CH3:30])(=[O:29])=[O:28])([CH2:13][CH2:14][N:15]1[CH:19]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:17]([CH3:26])=[N:16]1)[C:3]([NH:5][O:6]C1CCCCO1)=[O:4].CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>CCO>[OH:6][NH:5][C:3](=[O:4])[C@:2]([CH3:1])([S:27]([CH3:30])(=[O:29])=[O:28])[CH2:13][CH2:14][N:15]1[CH:19]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:17]([CH3:26])=[N:16]1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 86710235(2R)-2-methyl-4-(3-methyl-4-phenyl-1H-pyrazol-1-yl)-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

Product 1

HCID 66558210(2R)-N-hydroxy-2-methyl-4-(3-methyl-4-phenyl-1H-pyrazol-1-yl)-2-(methylsulfonyl)butanamideYield 36%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (2R)-2-methyl-4-(3-methyl-4-phenyl-1H-pyrazol-1-yl)-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (110 mg, 0.253 mmol) in EtOH (5 mL) was added PPTS (20 mg, 0.080 mmol) and the mixture was heated at reflux for 3 h. The solution was concentrated to afford a crude white solid which was purified via flash chromatography using an Analogix SF10-8 g silica column eluting with ethyl acetate in heptane (50-80%) to give (2R)—N-hydroxy-2-methyl-4-(3-methyl-4-phenyl-1H-pyrazol-1-yl)-2-(methylsulfonyl)butanamide (32 mg, 36% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ 7.54-7.25 (m, 1H), 4.39-4.21 (m, 2H), 3.04 (s, 3H), 2.91-2.77 (m, 1H), 2.59-2.46 (m, 1H), 2.43 (s, 3H), 1.71 (s, 3H). LC-MS M+H+352.1.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 3 h
  3. concentrationThe solution was concentrated
  4. customto afford a crude white solid which
  5. customwas purified via flash chromatography
  6. washeluting with ethyl acetate in heptane (50-80%)

Sources & evidence

ORD record
ord-791d681f54a343ebae7a7661844393a5
Source dataset
uspto-grants-2014_08
Patent number
US08809333B2

Reaction notes

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