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Cesium carbonate → tert-butyl ((3R)-3-hydroxy-3-(3-((6-oxopiperidin-2-yl)methoxy)phenyl)propyl)carbamate

HRID 2277071
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HRID 2277071 반응식
CS([O:5][CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][C:9](=[O:13])[NH:8]1)(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+].[OH:20][C@@H:21]([C:32]1[CH:37]=[CH:36][CH:35]=[C:34](O)[CH:33]=1)[CH2:22][CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28]>CN(C=O)C>[OH:20][C@@H:21]([C:32]1[CH:33]=[CH:34][CH:35]=[C:36]([O:5][CH2:6][CH:7]2[CH2:12][CH2:11][CH2:10][C:9](=[O:13])[NH:8]2)[CH:37]=1)[CH2:22][CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 90404452(6-Oxopiperidin-2-yl)methyl methanesulfonateHCID 90405310(R)-tert-butyl 3-hydroxy-3-(3-hydroxyphenyl)propylcarbamate2회

생성물 1

HCID 131733447tert-butyl ((3R)-3-hydroxy-3-(3-((6-oxopiperidin-2-yl)methoxy)phenyl)propyl)carbamate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a mixture of (6-oxopiperidin-2-yl)methyl methanesulfonate (0.44 g, 2.2 mmol) in DMF (15 ml) was added Cs2CO3 (3.5 g, 11 mmol) and phenol (Intermediate I) (0.88 g, 3.3 mmol). The reaction mixture was stirred at room temperature for 40 hours and partitioned between water and ethyl acetate. Organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. Purification by flash chromatography (20% MeOH-EtOAc) gave tert-butyl ((3R)-3-hydroxy-3-(3-((6-oxopiperidin-2-yl)methoxy)phenyl)propyl)carbamate as a yellow oil. Yield (0.17 g, 20%); 1H NMR (400 MHz, CD3OD) δ 7.24 (t, J=8.0 Hz, 1H), 6.97-6.93 (m, 2H), 6.84 (d, J=8.0 Hz, 1H), 4.64 (t, J=7.2 Hz, 1H), 4.06-4.02 (m, 1H), 3.94-3.90 (m, 1H), 3.86-3.76 (m, 1H), 3.15-3.06 (m, 2H), 2.37-2.30 (m, 2H), 2.05-1.92 (m, 3H), 1.86-1.75 (m, 3H), 1.43 (s, 9H).

후처리

  1. custompartitioned between water and ethyl acetate
  2. washOrganic layer was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash chromatography (20% MeOH-EtOAc)

출처 및 근거

ORD 기록
ord-808a63fdd61a4ac3b35e8742dff2be1d
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09133154B2

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