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Potassium Carbonate → tert-butyl [(1S)-2-({1-[6-(2-cyclopropylethoxy)-1,3-benzoxazol-2-yl]piperidin-4-yl}oxy)-1-methylethyl]carbamate

HRID 2368119
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HRID 2368119 반응식
[CH:1]1([CH2:4][CH2:5][OH:6])[CH2:3][CH2:2]1.CS(Cl)(=O)=O.O[C:13]1[CH:39]=[CH:38][C:16]2[N:17]=[C:18]([N:20]3[CH2:25][CH2:24][CH:23]([O:26][CH2:27][C@@H:28]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH3:29])[CH2:22][CH2:21]3)[O:19][C:15]=2[CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.CN(C=O)C.C(OCC)(=O)C.C(N(CC)CC)C>[CH:1]1([CH2:4][CH2:5][O:6][C:13]2[CH:39]=[CH:38][C:16]3[N:17]=[C:18]([N:20]4[CH2:25][CH2:24][CH:23]([O:26][CH2:27][C@@H:28]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:34])([CH3:35])[CH3:36])[CH3:29])[CH2:22][CH2:21]4)[O:19][C:15]=3[CH:14]=2)[CH2:3][CH2:2]1
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참가 물질

9

반응물 4

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 1376422-Cyclopropylethan-1-olHCID 86658692tert-butyl [(1S)-2-{[1-(6-hydroxy-1,3-benzoxazol-2-yl)piperidin-4-yl]oxy}-1-methylethyl]carbamate

생성물 1

HCID 86658707tert-butyl [(1S)-2-({1-[6-(2-cyclopropylethoxy)-1,3-benzoxazol-2-yl]piperidin-4-yl}oxy)-1-methylethyl]carbamate수율 64.7%

시약·촉매·용매 4

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 2-cyclopropylethanol (550 mg) in THF (10 mL) were added triethylamine (0.80 mL) and methanesulfonyl chloride (0.50 mL), and the mixture was stirred at room temperature for 30 min. The reaction mixture was added to a suspension of tert-butyl [(1S)-2-{[1-(6-hydroxy-1,3-benzoxazol-2-yl)piperidin-4-yl]oxy}-1-methylethyl]carbamate (250 mg) and potassium carbonate (1.8 g) in DMF (10 mL), and the mixture was stirred at room temperature for 15 hr. The reaction mixture was diluted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (190 mg).

후처리

  1. stirringthe mixture was stirred at room temperature for 15 hr
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe obtained residue was purified by silica gel chromatography (hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-59c8b7366b874bbdaebd2bf7df6eacb3
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08703758B2

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