Boron tribromide → HCID 58065518, compound

HRID 909611Notes

Reaction equation

HRID 909611 reaction equation
C[O:2][CH2:3][C@H:4]([CH3:35])[O:5][C:6]1[CH:7]=[C:8]([C:23]2[NH:27][C:26]([C:28]3[O:29][C@@H:30]([CH3:34])[CH:31]([OH:33])[N:32]=3)=[CH:25][CH:24]=2)[CH:9]=[C:10]([O:12][C:13]2[CH:18]=[N:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][N:14]=2)[CH:11]=1.B(Br)(Br)Br.C(=O)([O-])O.[Na+]>C(Cl)Cl>[OH:2][CH2:3][C@H:4]([CH3:35])[O:5][C:6]1[CH:7]=[C:8]([C:23]2[NH:27][C:26]([C:28]3[O:29][C@@H:30]([CH3:34])[CH:31]([OH:33])[N:32]=3)=[CH:25][CH:24]=2)[CH:9]=[C:10]([O:12][C:13]2[CH:18]=[N:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][N:14]=2)[CH:11]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 58065450HCID 58065450, compound

Product 1

HCID 58065518HCID 58065518, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

(5S)-2-[5-(3-[(1S)-2-Methoxy-1-methylethoxy]-5-{[5-(methylsulfonyl)pyrazin-2-yl]oxy}phenyl)-1H-pyrrol-2-yl]-5-methyl-4,5-dihydro-1,3-oxazol-4-ol (410 mg, 0.816 mmol) synthesized in Example (103d) was dissolved in methylene chloride (20 mL), and cooled to −78° C. Boron tribromide (1.0 mol/L methylene chloride solution, 2.04 mL, 2.04 mmol) was added, and stirring was carried out for 2 hours with the temperature being raised gradually to room temperature. A saturated aqueous sodium hydrogencarbonate solution (20 mL) was added, and extraction was carried out twice with methylene chloride (20 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: methanol/methylene chloride=2%-10%) to afford the desired product (362 mg, yield 91%) as a white solid.

Workup

  1. temperaturebeing raised gradually to room temperature
  2. extractionextraction
  3. washThe organic layer was washed with saturated brine
  4. dry with materialsubsequently dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified
  7. washsilica gel column chromatography (elution solvent: methanol/methylene chloride=2%-10%)

Sources & evidence

ORD record
ord-23e005c84f18484b9e5e10b2cfbd86f3
Source dataset
uspto-grants-2011_09
Patent number
US08017610B2

Reaction notes

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