Boron Trichloride → HCID 136365557, compound

HRID 1951610Notes

Reaction equation

HRID 1951610 reaction equation
[CH:1]([C:4]1[O:8][C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15]C)=[N:6][C:5]=1[CH2:17][CH2:18][C:19]([C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[C:23]([CH3:33])[CH:22]=1)=[O:20])([CH3:3])[CH3:2].ClB(Cl)Cl>C(Cl)Cl>[CH:1]([C:4]1[O:8][C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[OH:15])=[N:6][C:5]=1[CH2:17][CH2:18][C:19]([C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[C:23]([CH3:33])[CH:22]=1)=[O:20])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 69004823HCID 69004823, compound

Product 1

HCID 136365557HCID 136365557, compoundYield 17.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 3-[4-[3-[5-isopropyl-2-(2-methoxyphenyl)-4-oxazolyl]propionyl]-2-methylphenyl]propionate (24 mg, 0.0534 mmol) was dissolved in methylene chloride (1.2 mL) 1M dichloromethane solution of trichloroborane (127 μL, 0.127 mmol) was added to the solution at 0° C. The mixture was stirred at room temperature for 24 hours. Ice-cold water (5 mL) was added to the mixture. The resulting mixture was extracted with chloroform. The organic layer was washed with saturated aqueous solution of sodium carbonate and water, and dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography with hexane/ethyl acetate (3:1, v/v) to give the desired compound (4 mg) as white crystalline product (yield 17%).

Workup

  1. additionwas added to the solution at 0° C
  2. extractionThe resulting mixture was extracted with chloroform
  3. washThe organic layer was washed with saturated aqueous solution of sodium carbonate and water
  4. dry with materialdried with anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography with hexane/ethyl acetate (3:1

Sources & evidence

ORD record
ord-b5dbebc1c0df4482af25b3165ee544aa
Source dataset
uspto-grants-2013_03
Patent number
US08404726B2

Reaction notes

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