Hydrochloric Acid → HCID 66558213, compound

HRID 2405929Notes

Reaction equation

HRID 2405929 reaction equation
[CH3:1][C@@:2]([S:26]([CH3:29])(=[O:28])=[O:27])([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)[CH:17]=[N:16]1)[C:3]([NH:5][O:6]C1CCCCO1)=[O:4].Cl>C1COCC1>[OH:6][NH:5][C:3](=[O:4])[C@:2]([CH3:1])([S:26]([CH3:29])(=[O:28])=[O:27])[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)[CH:17]=[N:16]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86710240HCID 86710240, compound

Product 1

HCID 66558213HCID 66558213, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2R)-2-methyl-2-(methylsulfonyl)-4-(4-phenyl-1H-pyrazol-1-yl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (0.685 g, 1.62 mmol, 1 eq) in THF (20 mL) was added HCl (4M aq. sol.) and the reaction was allowed to stir at RT overnight. The reaction mixture was concentrated and azeotroped with MeOH to remove water to give (2R)—N-hydroxy-2-methyl-2-(methylsulfonyl)-4-(4-phenyl-1H-pyrazol-1-yl)butanamide (497 mg, 91% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 10.85-10.73 (m, 1H), 10.30-10.18 (m, 1H), 8.19 (s, 1H), 7.86 (s, 1H), 7.60-7.50 (m, 2H), 7.32 (t, J=7.7 Hz, 2H), 7.15 (s, 1H), 4.27-4.14 (m, 1H), 4.10-3.95 (m, 1H), 3.04 (s, 3H), 2.79-2.63 (m, 1H), 2.32-2.18 (m, 1H), 1.46 (s, 3H). LC-MS M+H+338.0.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customazeotroped with MeOH
  3. customto remove water

Sources & evidence

ORD record
ord-476c1a3986b940fd8f8dbda27564cd34
Source dataset
uspto-grants-2014_08
Patent number
US08809333B2

Reaction notes

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