Hydrochloric Acid → (2R)-N-hydroxy-4-[4-{4-[(4-hydroxycyclohexyl)oxy]phenyl}-2-oxopyridin-1(2H)-yl]-2-methyl-2-(methylsulfonyl)butanamide

HRID 709209Notes

Reaction equation

HRID 709209 reaction equation
Cl.[OH:2][CH:3]1[CH2:8][CH2:7][CH:6]([O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][N:19]([CH2:22][CH2:23][C@@:24]([CH3:39])([S:35]([CH3:38])(=[O:37])=[O:36])[C:25]([NH:27][O:28]C4CCCCO4)=[O:26])[C:18](=[O:40])[CH:17]=3)=[CH:12][CH:11]=2)[CH2:5][CH2:4]1>O1CCOCC1>[OH:28][NH:27][C:25](=[O:26])[C@:24]([CH3:39])([S:35]([CH3:38])(=[O:37])=[O:36])[CH2:23][CH2:22][N:19]1[CH:20]=[CH:21][C:16]([C:13]2[CH:12]=[CH:11][C:10]([O:9][CH:6]3[CH2:5][CH2:4][CH:3]([OH:2])[CH2:8][CH2:7]3)=[CH:15][CH:14]=2)=[CH:17][C:18]1=[O:40]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86671918(2R)-4-[4-{4-[(4-hydroxycyclohexyl)oxy]phenyl}-2-oxopyridin-1(2H)-yl]-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

Product 1

HCID 86671917(2R)-N-hydroxy-4-[4-{4-[(4-hydroxycyclohexyl)oxy]phenyl}-2-oxopyridin-1(2H)-yl]-2-methyl-2-(methylsulfonyl)butanamideYield 54%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

HCl (1.0 N in water, 2.37 mL) was added to a solution of the (2R)-4-[4-{4-[(4-hydroxycyclohexyl)oxy]phenyl}-2-oxopyridin-1(2H)-yl]-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (444 mg, 0.789 mmol) in 1,4-dioxane (5 mL). After 1 hour the reaction was concentrated to give a brown solid. The solid was triturated with ethanol at 50° C., for 30 minutes. After cooling, filtration afforded the title compound as a white solid (203 mg, 54%). LCMS m/z 479.7 (M+1)

Workup

  1. concentrationAfter 1 hour the reaction was concentrated
  2. customto give a brown solid
  3. customThe solid was triturated with ethanol at 50° C., for 30 minutes
  4. temperatureAfter cooling
  5. filtrationfiltration

Sources & evidence

ORD record
ord-4d37c07939134f0dbbe67e734e13e0bc
Source dataset
uspto-grants-2015_11
Patent number
US09180123B2

Reaction notes

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