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Tetrahydrofuran → (2S,3R)-3-(formyloxy)-5-[4-(6-methoxypyridin-3-yl)phenyl]-2-[2-(4-oxo-1,2,3-benzotriazin-3(4H)-yl)ethyl]pentanoic acid

HRID 2410411
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HRID 2410411 반응식
[OH:1][C@@H:2]1[C@H:6]([OH:7])[O:5][C@H:4]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:17]=[N:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=3)=[CH:12][CH:11]=2)[C@@H:3]1[CH2:24][CH2:25][N:26]1[C:31](=[O:32])[C:30]2[CH:33]=[CH:34][CH:35]=[CH:36][C:29]=2[N:28]=[N:27]1.[O:37]1CCCC1.I([O-])(=O)(=O)=O.[Na+].[K]>C(O)(C)(C)C>[CH:6]([O:5][C@H:4]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:17]=[N:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)=[CH:12][CH:11]=1)[C@H:3]([CH2:24][CH2:25][N:26]1[C:31](=[O:32])[C:30]2[CH:33]=[CH:34][CH:35]=[CH:36][C:29]=2[N:28]=[N:27]1)[C:2]([OH:37])=[O:1])=[O:7]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 5462222PotassiumHCID 23667635Sodium periodateHCID 671825273-{2-[(2R,3R,4S,5R)-4,5-dihydroxy-2-{2-[4-(6-methoxypyridin-3-yl)phenyl]ethyl}tetrahydrofuran-3-yl]ethyl}-1,2,3-benzotriazin-4(3H)-one

생성물 1

HCID 86700968(2S,3R)-3-(formyloxy)-5-[4-(6-methoxypyridin-3-yl)phenyl]-2-[2-(4-oxo-1,2,3-benzotriazin-3(4H)-yl)ethyl]pentanoic acid

시약·촉매·용매 1

HCID 6386tert-Butanol용매

실험 절차

To a solution of the compound obtained from step d above (8 g) in tert-butanol:tetrahydrofuran (40 mL:40 mL) at 0° C., a solution of sodium metaperiodate (14 g in 40 mL of water) was added. The reaction mixture was stirred for 2 hours at the same temperature, and potassium permangnate (518 mg) was added at 0° C. After stirring the reaction mixture for an additional 6 hours at room temperature, the reaction mixture was evaporated on a rotary evaporator. The residue was taken into water and extracted with ethyl acetate. The organic layer was washed with water and brine solution and dried over anhydrous sodium sulphate. The solvent was evaporated under the reduced pressure, to afford the title compound (8 g).

후처리

  1. additionwas added at 0° C
  2. customthe reaction mixture was evaporated on a rotary evaporator
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and brine solution
  5. dry with materialdried over anhydrous sodium sulphate
  6. customThe solvent was evaporated under the reduced pressure

출처 및 근거

ORD 기록
ord-1f9bbe4aa9f34a76b328021345e8c495
출처 데이터셋
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08816073B2

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