Sodium Acetate → HCID 88995429, compound

HRID 1184017Notes

Reaction equation

HRID 1184017 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][N:13]([CH2:16][CH2:17][C:18]([CH3:27])([S:23]([CH3:26])(=[O:25])=[O:24])[C:19]([NH:21][OH:22])=[O:20])[C:12](=[O:28])[CH:11]=2)=[CH:6][CH:5]=1)(=O)[CH3:2].Cl.[CH3:30][O:31][NH2:32].C([O-])(=O)C.[Na+]>C(O)C>[OH:22][NH:21][C:19](=[O:20])[C:18]([CH3:27])([S:23]([CH3:26])(=[O:25])=[O:24])[CH2:17][CH2:16][N:13]1[CH:14]=[CH:15][C:10]([C:7]2[CH:8]=[CH:9][C:4](/[C:1](=[N:32]/[O:31][CH3:30])/[CH3:2])=[CH:5][CH:6]=2)=[CH:11][C:12]1=[O:28]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 866719684-(4-(4-Acetylphenyl)-2-oxopyridin-1(2h)-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide

Product 1

HCID 88995429HCID 88995429, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of 4-[4-(4-acetylphenyl)-2-oxopyridin-1(2H)-yl]-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide (105 mg, 0.258 mmol), O-methylhydroxylamine hydrochloride (86.2 mg, 1.03 mmol) and sodium acetate (107 mg, 1.03 mmol) in ethanol (10 mL, 0.025M) was heated in an oil bath at 70° C. for 3 hours. The volatiles were removed by rotary evaporation. The remaining material was redissolved in 1.5 mL DMSO and run on Shimadzu HPLC 30×100 mm reverse phase column. The material was eluted with 20-35% acetonitrile in water with 0.1% ammonium hydroxide modifier. The gradient was run for 8 min then held at 35% for an additional two minutes. The desired material eluted at about 30% acetonitrile. This solution was concentrated down by rotary evaporation yielding 90.7 mg (80.7%) of the title compound a white solid. LC/MS m/z 436 (M+1). 1H NMR (500 MHz, DMSO-d6) δ ppm 1.57 (s, 3H) 2.13-2.21 (m, 1H) 2.21 (s, 3H) 2.39-2.48 (m, 1H) 3.11 (s, 3H) 3.70-3.81 (m, 1H) 3.94 (s, 3H) 4.12 (td, J=11.90, 5.00 Hz, 1H) 6.68 (dd, J=7.20, 1.83 Hz, 1H) 6.75 (d, J=1.95 Hz, 1H) 7.71-7.82 (m, 5H) 9.27 (br. s., 1H) 11.14 (br. s., 1H)

Workup

  1. customThe volatiles were removed by rotary evaporation
  2. dissolutionThe remaining material was redissolved in 1.5 mL DMSO
  3. washThe material was eluted with 20-35% acetonitrile in water with 0.1% ammonium hydroxide modifier
  4. waitthen held at 35% for an additional two minutes
  5. washThe desired material eluted at about 30% acetonitrile
  6. concentrationThis solution was concentrated down by rotary evaporation

Sources & evidence

ORD record
ord-0f935695dcd84a86ba1555ca90656f47
Source dataset
uspto-grants-2014_03
Patent number
US08664401B2

Reaction notes

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