Hydrochloric Acid → HCID 66558211, compound

HRID 2405918Notes

Reaction equation

HRID 2405918 reaction equation
[CH:1]1([C:6]2[CH:7]=[N:8][N:9]([CH2:11][CH2:12][C@@:13]([CH3:28])([S:24]([CH3:27])(=[O:26])=[O:25])[C:14]([NH:16][O:17]C3CCCCO3)=[O:15])[CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl>O1CCOCC1.C(Cl)Cl.O>[CH:1]1([C:6]2[CH:7]=[N:8][N:9]([CH2:11][CH2:12][C@@:13]([CH3:28])([S:24]([CH3:27])(=[O:25])=[O:26])[C:14]([NH:16][OH:17])=[O:15])[CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 86710233HCID 86710233, compound

Product 1

HCID 66558211HCID 66558211, compoundYield 5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of (2R)-4-(4-cyclopentyl-1H-pyrazol-1-yl)-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (100 mg, 0.242 mmol) in dioxane (2 mL), DCM (2 mL) and water (500 uL) was added a 4.0M sol of HCl in dioxane (0.36 mL, 1.45 mmol). The reaction mixture was stirred at RT for 30 minutes. The solvent was removed and the crude mixture was purified by HPLC (Column: Phenomenex Luna (2) C18 150×3.0 mm 5μ; flow rate 0.75 mL/min; Gradient: 5-100% MeOH/Water containing 0.1% TFA) to give (2R)-4-(4-cyclopentyl-1H-pyrazol-1-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide (4 mg, 5% yield). LC-MS M+H+330.1.

Workup

  1. customThe solvent was removed
  2. customthe crude mixture was purified by HPLC (Column: Phenomenex Luna (2) C18 150×3.0 mm 5μ; flow rate 0.75 mL/min; Gradient: 5-100% MeOH/Water containing 0.1% TFA)

Sources & evidence

ORD record
ord-a0064e2881c145e7b23d1ee922e765a9
Source dataset
uspto-grants-2014_08
Patent number
US08809333B2

Reaction notes

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