Boron tribromide → HCID 10238624, compound

HRID 458124Notes

Reaction equation

HRID 458124 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12](=[O:35])[C:13]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)([OH:27])[CH2:14][C:15]([C:18]3[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=3[O:25]C)([CH3:17])[CH3:16])=[CH:8][CH:9]=2)[CH2:4][O:3]1.B(Br)(Br)Br>C(Cl)Cl>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12](=[O:35])[C:13]([CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)([OH:27])[CH2:14][C:15]([C:18]3[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=3[OH:25])([CH3:17])[CH3:16])=[CH:8][CH:9]=2)[CH2:4][O:3]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 10288784HCID 10288784, compound

Product 1

HCID 10238624HCID 10238624, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-benzyl-4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methylpentanoic acid (1-oxo-1,3-dihydroisobenzofuran-5-yl)amide (25 mg, 0.053 mmol) in anhydrous methylene chloride (1 mL) and cooled in ice was added boron tribromide (0.3 mL of 1 M solution in methylene chloride, 0.3 mmol). The reaction was stirred at room temperature for 3 hours and then quenched with water (5 mL). Methylene chloride (25 mL) was added, the organic layer separated, dried over anhydrous sodium sulfate and concentrated in vacuo to give a light brown oil which was purified by preparative TLC eluting with methylene chloride-EtOAc (9:1) to give the title compound as a light, cream colored solid.

Workup

  1. customquenched with water (5 mL)
  2. additionMethylene chloride (25 mL) was added
  3. customthe organic layer separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give a light brown oil which
  7. customwas purified by preparative TLC
  8. washeluting with methylene chloride-EtOAc (9:1)

Sources & evidence

ORD record
ord-c5466ff7c2d74998b467333d0157665d
Source dataset
uspto-grants-2007_03
Patent number
US07189758B2

Reaction notes

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