Hydrochloric Acid → (+/-)-4-[4-(1-Benzofuran-2-yl)-2-oxopyridin-1(2H)-yl]-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide

HRID 84258Notes

Reaction equation

HRID 84258 reaction equation
Cl.[O:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH:4]=[C:3]1[C:11]1[CH:16]=[CH:15][N:14]([CH2:17][CH2:18][C:19]([CH3:34])([S:30]([CH3:33])(=[O:32])=[O:31])[C:20]([NH:22][O:23]C2CCCCO2)=[O:21])[C:13](=[O:35])[CH:12]=1.O>O1CCOCC1.ClCCl>[O:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH:4]=[C:3]1[C:11]1[CH:16]=[CH:15][N:14]([CH2:17][CH2:18][C:19]([CH3:34])([S:30]([CH3:33])(=[O:31])=[O:32])[C:20]([NH:22][OH:23])=[O:21])[C:13](=[O:35])[CH:12]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 866719424-[4-(1-benzofuran-2-yl)-2-oxopyridin-1(2H)-yl]-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

Product 1

HCID 86671941(+/-)-4-[4-(1-Benzofuran-2-yl)-2-oxopyridin-1(2H)-yl]-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamideYield 99%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A 4.0 M solution of HCl in 1,4-dioxane (5 mL) was added slowly to a solution of (+/−)-4-[4-(1-benzofuran-2-yl)-2-oxopyridin-1(2H)-yl]-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (105 mg, 0.22 mmol) in dichloromethane (5 mL) with water (1.0 mL) at 0° C. The ice bath was removed and the reaction was allowed to warm to rt. After 30 min (complete by TLC), the reaction was concentrated to afford a crude white solid. The crude was triturated in isopropanol (5 mL) overnight. The solid was collected via filtration, washed with isopropanol (5 mL), isopropanol:heptane (1:1, 5 mL), heptane (5 mL), and ether (5 mL). The solid was collected by filteration and dried under vacuum to afford a white solid (86.1 mg, 99%). LC-MS m/z 405.5 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.57 (s, 3 H) 2.10-2.23 (m, 1 H) 2.39-2.48 (m, 1 H) 3.11 (s, 3 H) 3.71-3.81 (m, 1 H) 4.05-4.15 (m, 1 H) 6.78-6.89 (m, 2 H) 7.27-7.35 (m, 1 H) 7.37-7.45 (m, 1 H) 7.63-7.82 (m, 4 H).

Workup

  1. customThe ice bath was removed
  2. concentrationthe reaction was concentrated
  3. customto afford a crude white solid
  4. customThe crude was triturated in isopropanol (5 mL) overnight
  5. filtrationThe solid was collected via filtration
  6. washwashed with isopropanol (5 mL), isopropanol:heptane (1:1, 5 mL), heptane (5 mL), and ether (5 mL)
  7. customThe solid was collected by filteration
  8. customdried under vacuum

Sources & evidence

ORD record
ord-95b41a31b0154b6d95186f25f625042a
Source dataset
uspto-grants-2014_09
Patent number
US08846933B2

Reaction notes

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