Hydrochloric Acid → HCID 66558217, compound

HRID 2405942Notes

Reaction equation

HRID 2405942 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[N:12][N:13]([CH2:15][CH2:16][C@@:17]([CH3:32])([S:28]([CH3:31])(=[O:30])=[O:29])[C:18]([NH:20][O:21]C2CCCCO2)=[O:19])[CH:14]=1.Cl>CCO>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[N:12][N:13]([CH2:15][CH2:16][C@@:17]([CH3:32])([S:28]([CH3:31])(=[O:30])=[O:29])[C:18]([NH:20][OH:21])=[O:19])[CH:14]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86710247HCID 86710247, compound

Product 1

HCID 66558217HCID 66558217, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (2R)-4-[4-(1,3-benzoxazol-2-yl)-1H-pyrazol-1-yl]-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (0.410 g, 0.886 mmol) in EtOH (40 mL) was added 1M HCl (20 mL). The reaction mixture was allowed to stir at room temperature overnight. The reaction mixture was concentrated and was purified via reverse-phase chromatography, using 5%-95% acetonitrile/water with 0.1% formic acid modifier. The target fractions were combined and evaporated to give (2R)-4-[4-(1,3-benzoxazol-2-yl)-1H-pyrazol-1-yl]-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide (120 mg, 36% yield) as a light peach solid. 1H NMR (400 MHz, DMSO-d6) δ 1.50 (s, 3H) 2.21-2.40 (m, 1H) 2.70-2.87 (m, 1H) 3.06 (s, 3H) 4.03-4.21 (m, 1H) 4.26-4.51 (m, 1H) 7.27-7.44 (m, 2H) 7.63-7.78 (m, 2H) 8.14 (s, 1H) 8.64 (s, 1H) 9.23 (br. s., 1H) 10.99 (br. s., 1H) LC-MS M+H+379.1.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customwas purified via reverse-phase chromatography
  3. customevaporated

Sources & evidence

ORD record
ord-a67f356aae7c47249a8cf5de69105fa5
Source dataset
uspto-grants-2014_08
Patent number
US08809333B2

Reaction notes

Loading…