Hydrochloric Acid → HCID 66558212, compound

HRID 2405926Notes

Reaction equation

HRID 2405926 reaction equation
[CH3:1][C@@:2]([S:21]([CH3:24])(=[O:23])=[O:22])([CH2:13][CH2:14][N:15]1[CH:19]=[C:18]([CH3:20])[CH:17]=[N:16]1)[C:3]([NH:5][O:6]C1CCCCO1)=[O:4].Cl>ClCCl.CO.O1CCOCC1>[OH:6][NH:5][C:3](=[O:4])[C@:2]([CH3:1])([S:21]([CH3:24])(=[O:23])=[O:22])[CH2:13][CH2:14][N:15]1[CH:19]=[C:18]([CH3:20])[CH:17]=[N:16]1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 86710238HCID 86710238, compound

Product 1

HCID 66558212HCID 66558212, compoundYield 34.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (2R)-2-methyl-4-(4-methyl-1H-pyrazol-1-yl)-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (19 mg, 0.053 mmol, 0.5 eq) in dichloromethane (0.5 mL) and MeOH (0.1 mL) was added a 4.0 M solution of HCl in 1,4-dioxane (0.5 mL). The reaction was allowed to stir for 1 h. The solvent was removed under reduced pressure. The crude material was triturated in pentane/Et2O. The product was filtered, washed with heptane, and dried under reduced pressure to provide (2R)—N-hydroxy-2-methyl-4-(4-methyl-1H-pyrazol-1-yl)-2-(methylsulfonyl)butanamide as an off-white solid (5 mg). 1H NMR (400 MHz, DMSO-d6) δ 7.51-7.43 (m, 1H), 7.24-7.17 (m, 1H), 3.74-3.60 (m, 1H), 3.51-3.41 (m, 1H), 3.02 (s, 3H), 2.70-2.54 (m, 1H), 2.21-2.06 (m, 1H), 1.92 (s, 3H), 1.42 (s, 3H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe crude material was triturated in pentane/Et2O
  3. filtrationThe product was filtered
  4. washwashed with heptane
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-0678ecf13dd7465396896a9e51ec37a9
Source dataset
uspto-grants-2014_08
Patent number
US08809333B2

Reaction notes

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