Ethyl Acetate → 3-(2,6-Dichloro-purin-9-yl)-5-(4-ethyl-[1,2,3]triazol-1-yl)-cyclopentane-1,2-diol

HRID 215856노트

반응식

HRID 215856 반응식
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[CH2:15][C@H:14]([N:16]3[CH:20]=[C:19]([CH2:21][CH3:22])[N:18]=[N:17]3)C=C2)=[C:4]([Cl:23])[N:3]=1.I([O-])(=O)(=O)=O.[Na+].S(S([O-])=O)([O-])(=O)=[O:31].[Na+].[Na+].CCO[C:42]([CH3:44])=[O:43]>CC#N.O.[Ru](Cl)(Cl)Cl>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]2[CH2:15][CH:14]([N:16]3[CH:20]=[C:19]([CH2:21][CH3:22])[N:18]=[N:17]3)[CH:44]([OH:31])[CH:42]2[OH:43])=[C:4]([Cl:23])[N:3]=1

참가 물질

8

반응물 4

HCID 8857Ethyl AcetateHCID 656671Sodium PyrosulfiteHCID 23667635Sodium periodateHCID 86643670HCID 86643670, 화합물

생성물 1

HCID 866436713-(2,6-Dichloro-purin-9-yl)-5-(4-ethyl-[1,2,3]triazol-1-yl)-cyclopentane-1,2-diol

시약·촉매·용매 3

HCID 61850Ruthenium trichloride촉매HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

A solution of 2,6-dichloro-9-[(1R,4S)-4-(4-ethyl-[1,2,3]triazol-1-yl)-cyclopent-2-enyl]-9H-purine (1.442 g, 4.12 mmol) in EtOAc (15 mL) and MeCN (15 mL) is treated with a solution of ruthenium trichloride (0.120 g, 0.58 mmol) and sodium periodate (1.32 g, 6.18 mmol) in water (5 mL). The reaction mixture is stirred vigorously for 6 hours and then treated with sodium metabisulfite (saturated aqueous solution, 25 mL) and then stirred overnight. The resulting mixture is partitioned between water and EtOAc and the aqueous portion is extracted with EtOAc. The combined organic portions are washed with water, dried (MgSO4) and concentrated in vacuo. The crude product is purified by chromatography on silica eluting with 0-100% EtOAc in iso-hexane to afford the title compound as an oil orange solid. (MH+ 350).

후처리

  1. stirringstirred overnight
  2. customThe resulting mixture is partitioned between water and EtOAc
  3. extractionthe aqueous portion is extracted with EtOAc
  4. washThe combined organic portions are washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude product is purified by chromatography on silica eluting with 0-100% EtOAc in iso-hexane

출처 및 근거

ORD 기록
ord-f73be1695a244856b9cdda36e038daed
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193164B2

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