Hydrochloric Acid → (2R)-4-{5-Fluoro-2-oxo-4-[4-(2H-tetrazol-2-yl)phenyl]pyridin-1(2H)-yl}-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide

HRID 1625021Notes

Reaction equation

HRID 1625021 reaction equation
Cl.[F:2][C:3]1[C:4]([C:28]2[CH:33]=[CH:32][C:31]([N:34]3[N:38]=[N:37][CH:36]=[N:35]3)=[CH:30][CH:29]=2)=[CH:5][C:6](=[O:27])[N:7]([CH2:9][CH2:10][C@@:11]([CH3:26])([S:22]([CH3:25])(=[O:24])=[O:23])[C:12]([NH:14][O:15]C2CCCCO2)=[O:13])[CH:8]=1>ClCCl.CO>[F:2][C:3]1[C:4]([C:28]2[CH:29]=[CH:30][C:31]([N:34]3[N:38]=[N:37][CH:36]=[N:35]3)=[CH:32][CH:33]=2)=[CH:5][C:6](=[O:27])[N:7]([CH2:9][CH2:10][C@@:11]([CH3:26])([S:22]([CH3:25])(=[O:23])=[O:24])[C:12]([NH:14][OH:15])=[O:13])[CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86670636(2R)-4-{5-Fluoro-2-oxo-4-[4-(2H-tetrazol-2-yl)phenyl]pyridin-1(2H)-yl}-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

Product 1

HCID 86711575(2R)-4-{5-Fluoro-2-oxo-4-[4-(2H-tetrazol-2-yl)phenyl]pyridin-1(2H)-yl}-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamideYield 80.3%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Hydrochloric acid (4.0 M in 1,4-dioxane, 1.7 mL, 6.63 mmol) was added to a solution of (2R)-4-{5-fluoro-2-oxo-4-[4-(2H-tetrazol-2-yl)phenyl]pyridin-1(2H)-yl}-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (500 mg, 0.94 mmol) in dichloromethane:methanol (5:1, 6 mL) at room temperature. The reaction was stirred for 1 h then was concentrated under reduced pressure affording a residue, which was triturated in diethyl ether:pentane (1:1) overnight. The solid was collected via filtration and dried under reduced pressure to afford the title compound as a solid (340 mg, 76%). MS (LCMS) m/z 451.0 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.56 (s, 3 H) 2.09-2.21 (m, 1 H) 2.42-2.45 (m, 1 H) 3.09 (s, 3 H) 3.78 (m, J=11.80, 11.80, 5.20 Hz, 1 H) 3.97-4.10 (m, 1 H) 6.63 (d, J=7.61 Hz, 1 H) 7.84 (dd, J=8.68, 1.66 Hz, 2 H) 8.00-8.15 (m, 3 H) 10.16 (s, 1 H) 11.08 (br. s., 1 H).

Workup

  1. concentrationthen was concentrated under reduced pressure
  2. customaffording a residue, which
  3. customwas triturated in diethyl ether:pentane (1:1) overnight
  4. filtrationThe solid was collected via filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-563ece7e9e534e869a1786229043800f
Source dataset
uspto-grants-2014_07
Patent number
US08779148B2

Reaction notes

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