Hydrochloric Acid → 2-Ethyl-N-hydroxy-2-(methylsulfonyl)-4-(2-oxo-4-phenylpyridin-1(2H)-yl)butanamide

HRID 709267Notes

Reaction equation

HRID 709267 reaction equation
Cl.[CH2:2]([C:4]([S:30]([CH3:33])(=[O:32])=[O:31])([CH2:15][CH2:16][N:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:19][C:18]1=[O:29])[C:5]([NH:7][O:8]C1CCCCO1)=[O:6])[CH3:3]>ClCCl.CO>[CH2:2]([C:4]([S:30]([CH3:33])(=[O:32])=[O:31])([CH2:15][CH2:16][N:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:19][C:18]1=[O:29])[C:5]([NH:7][OH:8])=[O:6])[CH3:3]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 866719552-Ethyl-2-(methylsulfonyl)-4-(2-oxo-4-phenylpyridin-1(2H)-yl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

Product 1

HCID 866719562-Ethyl-N-hydroxy-2-(methylsulfonyl)-4-(2-oxo-4-phenylpyridin-1(2H)-yl)butanamideYield 27%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of hydrochloric acid (0.5 mL, 4.0 M in 1,4-dioxane) was added dropwise to a solution of 2-ethyl-2-(methylsulfonyl)-4-(2-oxo-4-phenylpyridin-1(2H)-yl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (45 mg, 0.1 mmol) in dichloromethane (0.5 mL) and methanol (0.1 mL) at 0° C. After 2 h, the reaction was concentrated under reduced pressure. The resulting residue was triturated with diethyl ether, filtered, washed with heptane, and dried under reduced pressure to provide an off-white solid (10 mg, 27%). MS (LCMS) m/z 379.5 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 0.97 (t, J=7.5 Hz, 3H), 1.86-1.95 (m, 1H), 2.31-2.45 (m, 3H), 3.29 (s, 3H), 3.99-4.08 (m 1H), 4.53-4.63 (m, 1H), 6.69 (br d, J=5.6 Hz, 1H), 6.99 (br s, 1H), 7.44-7.49 (m, 4H), 7.55-7.60 (m, 2H).

Workup

  1. concentrationthe reaction was concentrated under reduced pressure
  2. customThe resulting residue was triturated with diethyl ether
  3. filtrationfiltered
  4. washwashed with heptane
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-fc5c23fcab69438bae1f4d46edaa2d77
Source dataset
uspto-grants-2015_11
Patent number
US09180123B2

Reaction notes

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