Boron tribromide → HCID 58198506, compound

HRID 545314Notes

Reaction equation

HRID 545314 reaction equation
[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11](=[O:26])[C:12]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24]C)=[CH:20][CH:19]=2)(=[O:17])=[O:16])([CH3:14])[CH3:13])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11](=[O:26])[C:12]([S:15]([C:18]2[CH:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=2)(=[O:17])=[O:16])([CH3:14])[CH3:13])[CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 59662655HCID 59662655, compound

Product 1

HCID 58198506HCID 58198506, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 203 mg (0.53 mmol) of N-(5-tert-butyl-isoxazol-3-yl)-2-(4-methoxybenzenesulfonyl)-2-methyl-propionamide (Example 43, Table 19, prepared according to method A) in DCM (5 mL) were added 0.3 mL (3.18 mmol) of BBr3 at 0° C. under nitrogen atmosphere. The reaction was allowed to warm to room temperature and stirred for 18 h. The reaction was poured onto a saturated aqueous NaHCO3 solution-ice mixture (20 mL). The aqueous mixture was acidified to pH 5 and extracted with DCM (3×15 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was further purified by column chromatography (silica, eluent DCM, 0-20% ethyl acetate) to afford 64 mg of N-(5-tert-butyl-isoxazol-3-yl)-2-(4-hydroxy-benzenesulfonyl)-2-methyl-propionamide.

Workup

  1. extractionextracted with DCM (3×15 mL)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was further purified by column chromatography (silica, eluent DCM, 0-20% ethyl acetate)

Sources & evidence

ORD record
ord-3d12832eb8ba4500b30db43aa9a60d14
Source dataset
uspto-grants-2011_05
Patent number
US07935715B2

Reaction notes

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