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Ethyl Acetate → benzyl (R)-2-[3-[N-(benzoxazol-2-yl)-N-(3-(4-methoxyphenoxy)propyl)aminomethyl]phenoxy]butyrate

HRID 1712174
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HRID 1712174 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([OH:30])[CH:25]=1)[CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].FC(F)(F)S(O[C@@H:43]([CH2:54][CH3:55])[C:44]([O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:45])(=O)=O.C(OCC)(=O)C>C(#N)C>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:23][C:24]1[CH:25]=[C:26]([CH:27]=[CH:28][CH:29]=1)[O:30][C@H:43]([CH2:54][CH3:55])[C:44]([O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:45])[CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 219497323-((Benzo[d]oxazol-2-yl(3-(4-methoxyphenoxy)propyl)amino)methyl)phenolHCID 86622523benzyl (S)-2-trifluoromethanesulfonyloxybutyrate

생성물 1

HCID 11856279benzyl (R)-2-[3-[N-(benzoxazol-2-yl)-N-(3-(4-methoxyphenoxy)propyl)aminomethyl]phenoxy]butyrate수율 98.3%

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

To a solution of N-(benzoxazol-2-yl)-N-(3-(4-methoxyphenoxy)propyl)-3-hydrox ybenzylamine (52 mg) in acetonitrile (5 mL), potassium carbonate (18 mg) in a powder form was added at room temperature, and the resulting mixture was stirred for 10 minutes. A solution of benzyl (S)-2-trifluoromethanesulfonyloxybutyrate (50 mg) in acetonitrile (2 mL) was added dropwise to the reaction liquor, and the mixture was stirred at the same temperature for 18 hours. Ethyl acetate (50 mL) was added to the reaction liquor, and the mixture was washed with water and saturated brine, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1) to obtain a colorless oil (73 mg, 98.3%).

후처리

  1. stirringthe mixture was stirred at the same temperature for 18 hours
  2. washthe mixture was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1)

출처 및 근거

ORD 기록
ord-9a19163d6c99403286ab97b4d412c5f8
출처 데이터셋
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07790903B2

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