Boron tribromide → HCID 86668782, compound

HRID 533566Notes

Reaction equation

HRID 533566 reaction equation
B(Br)(Br)Br.[F:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][C:20]([CH3:29])([S:25]([CH3:28])(=[O:27])=[O:26])[C:21]([NH:23][OH:24])=[O:22])=[C:14]([O:30]C)[CH:13]=2)=[CH:8][CH:7]=1>ClCCl.O>[F:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][C:20]([CH3:29])([S:25]([CH3:28])(=[O:26])=[O:27])[C:21]([NH:23][OH:24])=[O:22])=[C:14]([OH:30])[CH:13]=2)=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 86668783HCID 86668783, compound

Product 1

HCID 86668782HCID 86668782, compoundYield 17.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (750 ul, 0.75 mmol, 1.0 M in dichloromethane) was added to a solution of (+/−)-4-(4′-fluoro-3-methoxybiphenyl-4-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide prepared as in Example 18 (154 mg, 0.389 mmol) in dichloromethane (10 mL) at 0° C. The reaction was allowed to warm to rt and stirred until complete, then was diluted with water (60 mL) and extracted with ethyl acetate (3×60 mL). The combined organics were dried (MgSO4), filtered and concentrated in vacuo. The solid was dissolved in 1N aqueous NaOH (60 mL), washed with ethyl acetate (3×80 mL), acidified using 1N aqueous HCl, and extracted with ethyl acetate (3×100 mL). The combined organics were dried (MgSO4), filtered, and concentrated in vacuo to afford the title compound as an off-white solid (25.4 mg, 17.1%). LC-MS m/z 382.5 (M+1). 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.68 (s, 3H) 2.12-2.23 (m, 1H) 2.41-2.55 (m, 2H) 2.74-2.90 (m, 1H) 3.07 (s, 3H) 6.97-7.03 (m, 2H) 7.10-7.20 (m, 3H) 7.53-7.60 (m, 2H).

Workup

  1. extractionextracted with ethyl acetate (3×60 mL)
  2. dry with materialThe combined organics were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. dissolutionThe solid was dissolved in 1N aqueous NaOH (60 mL)
  6. washwashed with ethyl acetate (3×80 mL)
  7. extractionextracted with ethyl acetate (3×100 mL)
  8. dry with materialThe combined organics were dried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-484a1451cfe24a4cbb694091fb68d6f9
Source dataset
uspto-grants-2014_10
Patent number
US08853258B2

Reaction notes

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