Hydrochloric Acid → N-hydroxy-2-methyl-2-(methylsulfonyl)-4-(4-phenyl-1H-imidazol-1-yl)butanamide

HRID 2405954Notes

Reaction equation

HRID 2405954 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)[N:17]=[CH:16]1)[C:3]([NH:5][O:6]C1CCCCO1)=[O:4].Cl.O1CCOCC1.CO>C(Cl)Cl>[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)[N:17]=[CH:16]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 312751,4-DioxaneHCID 867102522-methyl-2-(methylsulfonyl)-4-(4-phenyl-1H-imidazol-1-yl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

Product 1

HCID 86710253N-hydroxy-2-methyl-2-(methylsulfonyl)-4-(4-phenyl-1H-imidazol-1-yl)butanamideYield 41.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methyl-2-(methylsulfonyl)-4-(4-phenyl-1H-imidazol-1-yl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (24.3 mg, 0.058 mmol, 1 eq) in DCM (4 mL) was added 4M HCl in dioxane (0.290 mL, 1.16 mmol, 20 eq). The reaction mixture was allowed to stir at RT for 5 mins. MeOH (100 uL) was added to the mixture. The mixture was then concentrated to dryness to give N-hydroxy-2-methyl-2-(methylsulfonyl)-4-(4-phenyl-1H-imidazol-1-yl)butanamide (8.1 mg, 37% yield). LC-MS M+H+338.5.

Workup

  1. concentrationThe mixture was then concentrated to dryness

Sources & evidence

ORD record
ord-5473f4b2681e4892842427ad3b21b671
Source dataset
uspto-grants-2014_08
Patent number
US08809333B2

Reaction notes

Loading…