[(3aR,4R,6R,6aS)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]methyl acetate → [(3aR,4R,6R,6aS)-6-(6-isobutyl-9H-purin-9-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]methyl acetate

HRID 552725

반응식

HRID 552725 반응식
[C:1]([O:4][CH2:5][C@@H:6]1[C@@H:13]2[C@@H:9]([O:10][C:11]([CH3:15])([CH3:14])[O:12]2)[C@H:8]([N:16]2[CH:24]=[N:23][C:22]3[C:17]2=[N:18][CH:19]=[N:20][C:21]=3Cl)[CH2:7]1)(=[O:3])[CH3:2].[Br-].[CH2:27]([Zn+])[CH:28]([CH3:30])[CH3:29]>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:4][CH2:5][C@@H:6]1[C@@H:13]2[C@@H:9]([O:10][C:11]([CH3:15])([CH3:14])[O:12]2)[C@H:8]([N:16]2[CH:24]=[N:23][C:22]3[C:17]2=[N:18][CH:19]=[N:20][C:21]=3[CH2:27][CH:28]([CH3:30])[CH3:29])[CH2:7]1)(=[O:3])[CH3:2]

참가 물질

5

반응물 2

HCID 86607316[(3aR,4R,6R,6aS)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]methyl acetateHCID 178448254HCID 178448254, 화합물

생성물 1

HCID 67165669[(3aR,4R,6R,6aS)-6-(6-isobutyl-9H-purin-9-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]methyl acetate수율 45%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
60 °C

실험 절차

To a solution of [(3aR,4R,6R,6aS)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]methyl acetate (250.0 mg, 0.68 mmol) in degassed THF (6 mL) under nitrogen was added Pd(PPh3)4 (44 mg, 0.038 mmol) followed by 0.5 M of isobutylzinc bromide in tetrahydrofuran (2.04 mL) dropwise over 15 min. The reaction was heated at 60° C. for 1 hour. The reaction was cooled then quenched with saturated aq NH4Cl, extracted with EtOAc and the organic phase was washed with saturated aq EDTA.Na2 solution then water. The organic phase was concentrated and the residue purified by flash chromatography (0 to 100% EtOAc/DCM) to provide the title compound (120 mg, 45%).

후처리

  1. temperatureThe reaction was cooled
  2. customthen quenched with saturated aq NH4Cl
  3. extractionextracted with EtOAc
  4. washthe organic phase was washed with saturated aq EDTA
  5. concentrationThe organic phase was concentrated
  6. customthe residue purified by flash chromatography (0 to 100% EtOAc/DCM)

출처 및 근거

ORD 기록
ord-e2a4ea5ed84744fba7c1d2065205bbe5
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07951810B2

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