Boron tribromide → (2S)-2-[3-(5-{(4S)-4-[(1R)-1-Hydroxyethyl]-4,5-dihydro-1,3-oxazol-2-yl}-1H-pyrrol-2-yl)-5-{[5-(methylsulfonyl)pyrazin-2-yl]oxy}phenoxy]propan-1-ol

HRID 1964698노트

반응식

HRID 1964698 반응식
C[O:2][CH2:3][C@@H:4]([O:6][C:7]1[CH:8]=[C:9]([C:24]2[NH:28][C:27]([C:29]3[O:30][CH2:31][C@@H:32]([CH:34]([OH:36])[CH3:35])[N:33]=3)=[CH:26][CH:25]=2)[CH:10]=[C:11]([O:13][C:14]2[CH:19]=[N:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][N:15]=2)[CH:12]=1)[CH3:5].B(Br)(Br)Br.C(=O)([O-])O.[Na+]>C(Cl)Cl>[OH:36][C@@H:34]([C@@H:32]1[CH2:31][O:30][C:29]([C:27]2[NH:28][C:24]([C:9]3[CH:8]=[C:7]([CH:12]=[C:11]([O:13][C:14]4[CH:19]=[N:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][N:15]=4)[CH:10]=3)[O:6][C@@H:4]([CH3:5])[CH2:3][OH:2])=[CH:25][CH:26]=2)=[N:33]1)[CH3:35]

참가 물질

5

반응물 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 86761804[(4S)-2-(5-(3-{[(2S)-1-Methoxypropan-2-yl]oxy}-5-{[5-(methylsulfonyl)pyrazin-2-yl]oxy}phenyl)-1H-pyrrol-2-yl]-4,5-dihydro-1,3-oxazol-4-yl}ethanol

생성물 1

HCID 58065463(2S)-2-[3-(5-{(4S)-4-[(1R)-1-Hydroxyethyl]-4,5-dihydro-1,3-oxazol-2-yl}-1H-pyrrol-2-yl)-5-{[5-(methylsulfonyl)pyrazin-2-yl]oxy}phenoxy]propan-1-ol수율 71%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(1R)-1-{[(4S)-2-(5-(3-{[(2S)-1-Methoxypropan-2-yl]oxy}-5-{[5-(methylsulfonyl)pyrazin-2-yl]oxy}phenyl)-1H-pyrrol-2-yl]-4,5-dihydro-1,3-oxazol-4-yl}ethanol (213 mg, 0.412 mmol) synthesized in Example (114d) was dissolved in methylene chloride (5.0 mL), and boron tribromide (1.0 mol/L methylene chloride solution, 0.80 mL, 0.80 mmol) was added dropwise at −78° C., followed by stirring at room temperature for 1.5 hours under nitrogen atmosphere. To this reaction solution, a saturated aqueous sodium hydrogencarbonate solution (10 mL) was added, and extraction was carried out with methylene chloride (20 mL). The organic layer was washed with 1N aqueous sodium hydroxide solution (10 mL), 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=4%-5%) to afford the desired compound (147 mg, yield 71%) as a white solid.

후처리

  1. extractionextraction
  2. washThe organic layer was washed with 1N aqueous sodium hydroxide solution (10 mL)
  3. dry with materialsubsequently dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified
  6. washsilica gel column chromatography (elution solvent: methanol/methylene chloride=4%-5%)

출처 및 근거

ORD 기록
ord-bc121cb8c3474a8baa44ca08937a8268
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415359B2

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