Hydrochloric Acid → 4-(3-Fluorobiphenyl-4-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide

HRID 533523Notes

Reaction equation

HRID 533523 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:5]=[CH:6][C:7]=1[CH2:8][CH2:9][C:10]([CH3:25])([S:21]([CH3:24])(=[O:23])=[O:22])[C:11]([NH:13][O:14]C1CCCCO1)=[O:12].Cl>ClCCl.O1CCOCC1>[F:1][C:2]1[CH:3]=[C:4]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:5]=[CH:6][C:7]=1[CH2:8][CH2:9][C:10]([CH3:25])([S:21]([CH3:24])(=[O:23])=[O:22])[C:11]([NH:13][OH:14])=[O:12]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 866687584-(3-Fluorobiphenyl-4-yl)-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

Product 1

HCID 513552984-(3-Fluorobiphenyl-4-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamideYield 17.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

4-(3-Fluorobiphenyl-4-yl)-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (170 mg, 0.382 mmol) was dissolved in 5 mL of dichloromethane at ambient temperature. To this solution was added 4M HCl (2.86 mL, 11.5 mmol) in dioxane and the solution was stirred at ambient temperature for 5 minutes. The reaction was quenched by the addition of 0.5 mL of methanol. After stirring for an additional 5 minutes, the reaction was concentrated in vacuo. Purification was performed using Shimadzu prep HPLC to provide the title compound (24.4 mg, 14.5%) LC-MS m/z 366.5 (M+1) 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.68 (s, 3H) 2.06-2.16 (m, 1H) 2.53-2.59 (m, 1H) 2.60-2.67 (m, 1H) 2.79-2.89 (m, 1H) 3.06 (s, 3H) 7.30-7.33 (m, 1H) 7.31-7.33 (m, 1H) 7.34-7.37 (m, 1H) 7.38 (d, J=3.12 Hz, 1H) 7.40-7.42 (m, 1H) 7.43-7.46 (m, 2H) 7.58-7.64 (m, 2H)

Workup

  1. customThe reaction was quenched by the addition of 0.5 mL of methanol
  2. stirringAfter stirring for an additional 5 minutes
  3. concentrationthe reaction was concentrated in vacuo
  4. customPurification

Sources & evidence

ORD record
ord-a210af8ecd584b67a1eb7130a54ac79a
Source dataset
uspto-grants-2014_10
Patent number
US08853258B2

Reaction notes

Loading…