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Ethyl Acetate → tert-butyl [(1S)-2-{[1-(6-hydroxy-1,3-benzoxazol-2-yl)piperidin-4-yl]oxy}-1-methylethyl]carbamate

HRID 2368062
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HRID 2368062 반응식
[CH3:1][C@H:2]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:3][O:4][CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.C(N(CC)C(C)C)(C)C.Cl[C:29]1[O:30][C:31]2[CH:37]=[C:36]([OH:38])[CH:35]=[CH:34][C:32]=2[N:33]=1.C(OCC)(=O)C>CN(C=O)C>[OH:38][C:36]1[CH:35]=[CH:34][C:32]2[N:33]=[C:29]([N:8]3[CH2:9][CH2:10][CH:5]([O:4][CH2:3][C@@H:2]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH3:1])[CH2:6][CH2:7]3)[O:30][C:31]=2[CH:37]=1
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참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 234412462-Chloro-1,3-benzoxazol-6-OLHCID 57517479tert-butyl [(1S)-1-methyl-2-(piperidin-4-yloxy)ethyl]carbamate

생성물 1

HCID 86658692tert-butyl [(1S)-2-{[1-(6-hydroxy-1,3-benzoxazol-2-yl)piperidin-4-yl]oxy}-1-methylethyl]carbamate수율 95.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of tert-butyl [(1S)-1-methyl-2-(piperidin-4-yloxy)ethyl]carbamate (308 mg) and N,N-diisopropylethylamine (0.311 mL) in DMF (2 mL) was added 2-chloro-1,3-benzoxazol-6-ol (202 mg), and the mixture was stirred at room temperature for 5 hr. Ethyl acetate was added to the reaction mixture, and the mixture was washed with saturated brine and dried over anhydrous sodium sulfate. The extract was applied to silica gel chromatography (NH, ethyl acetate), and concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (446 mg).

후처리

  1. washthe mixture was washed with saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel chromatography (hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-52b817c87b3d4d34b4332b288880853c
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08703758B2

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