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Sodium Bicarbonate → HCID 135977444, 화합물

HRID 1964612
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HRID 1964612 반응식
[N:1]1([C:5]([C:7]2[CH:36]=[CH:35][C:10]([O:11][C:12]3[CH:13]=[C:14]([C:24]4[NH:28][C:27]([C:29]5[O:30][C:31]([CH3:34])=[N:32][N:33]=5)=[CH:26][CH:25]=4)[CH:15]=[C:16]([O:18][C@@H:19]([CH3:23])[CH2:20][O:21]C)[CH:17]=3)=[C:9]([F:37])[CH:8]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1.B(Br)(Br)Br.ClCCl.C(=O)([O-])O.[Na+]>ClCCl>[N:1]1([C:5]([C:7]2[CH:36]=[CH:35][C:10]([O:11][C:12]3[CH:17]=[C:16]([CH:15]=[C:14]([C:24]4[NH:28][C:27]([C:29]5[O:30][C:31]([CH3:34])=[N:32][N:33]=5)=[CH:26][CH:25]=4)[CH:13]=3)[O:18][C@@H:19]([CH3:23])[CH2:20][OH:21])=[C:9]([F:37])[CH:8]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 22277759Boron tribromide dichloromethaneHCID 135977445HCID 135977445, 화합물

생성물 1

HCID 135977444HCID 135977444, 화합물수율 21%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

2-(5-{3-[4-(Azetidin-1-ylcarbonyl)-2-fluorophenoxy]-5-[(1S)-2-methoxy-1-methylethoxy]phenyl}-1H-pyrrol-2-yl)-5-methyl-1,3,4-oxadiazole (379.2 mg, 0.748 mmol) synthesized in Example (66i) was dissolved in dichloromethane (15 mL), and a boron tribromide/dichloromethane solution (1M, 750 μL, 0.75 mmol) was added at −78° C. under nitrogen atmosphere, followed by stirring at 0° C. for 3 hours. To the reaction solution, a saturated aqueous sodium hydrogencarbonate solution was added, and extraction was carried out with ethyl acetate. The organic layer was washed with saturated brine, and subsequently dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: methanol/dichloromethane=2%-8%) to afford the desired compound (76.9 mg, yield 21%) as a pale yellow solid.

후처리

  1. extractionextraction
  2. washThe organic layer was washed with saturated brine
  3. dry with materialsubsequently dried over sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified
  6. washsilica gel column chromatography (elution solvent: methanol/dichloromethane=2%-8%)

출처 및 근거

ORD 기록
ord-ba4084d6ef3c4dfb997bdbcf7f55611e
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08415359B2

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