Boron tribromide → HCID 86670656, compound

HRID 1625048Notes

Reaction equation

HRID 1625048 reaction equation
B(Br)(Br)Br.[F:5][C:6]1[C:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:8]([O:25]C)[C:9](=[O:24])[N:10]([CH2:12][CH2:13][C@@:14]([CH3:23])([S:19]([CH3:22])(=[O:21])=[O:20])[C:15]([NH:17][OH:18])=[O:16])[CH:11]=1>C(Cl)Cl>[F:5][C:6]1[C:7]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[C:8]([OH:25])[C:9](=[O:24])[N:10]([CH2:12][CH2:13][C@@:14]([CH3:23])([S:19]([CH3:22])(=[O:21])=[O:20])[C:15]([NH:17][OH:18])=[O:16])[CH:11]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 86670657HCID 86670657, compound

Product 1

HCID 86670656HCID 86670656, compoundYield 16.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (760 μL, 0.76 mmol, 1.0 M in dichloromethane) was added to a solution of (2R)-4-(5-fluoro-3-methoxy-2-oxo-4-phenylpyridin-1(2H)-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide (156 mg, 0.378 mmol) in DCM (16.0 mL) at 0° C. The reaction was allowed to warm to rt and stirred overnight. The reaction mixture was concentrated to afford a brown solid. The crude product was purified via prepratory HPLC to afford the title compound as a yellow solid (25.4 mg, 16.9%). MS (LCMS) m/z 399.0 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.59 (s, 3 H) 2.11-2.25 (m, 1 H) 3.07 (s, 1 H) 3.13 (s, 2 H) 3.70-3.88 (m, 1 H) 4.02-4.26 (m, 1 H) 7.11 (d, J=7.81 Hz, 1 H) 7.37-7.65 (m, 5 H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto afford a brown solid
  3. customThe crude product was purified via prepratory HPLC

Sources & evidence

ORD record
ord-520c0774d0b3423e85a215b84f214b1b
Source dataset
uspto-grants-2014_07
Patent number
US08779148B2

Reaction notes

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