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2,2-Dimethoxypropane → N6-benzoyl-2',3'-isopropylidene adenosine

HRID 552719
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HRID 552719 반응식
[OH:1][C@@H:2]1[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[CH:18]=[N:17][C:16]2[C:11]1=[N:12][CH:13]=[N:14][C:15]=2[NH:19][C:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CO[C:30](OC)([CH3:32])[CH3:31].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>CC(C)=O>[OH:9][CH2:8][C@@H:5]1[C@H:6]2[O:7][C:30]([CH3:32])([CH3:31])[O:1][C@H:2]2[C@H:3]([N:10]2[CH:18]=[N:17][C:16]3[C:11]2=[N:12][CH:13]=[N:14][C:15]=3[NH:19][C:20](=[O:27])[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[O:4]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 64952,2-DimethoxypropaneHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 11728391N6-Benzoyladenosine

생성물 1

HCID 10001645N6-benzoyl-2',3'-isopropylidene adenosine수율 59%

시약·촉매·용매 1

HCID 180
Acetone
용매

실험 절차

N-{9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-9H-purin-6-yl}benzamide (0.643 g, 1.73 mmol), 2,2-dimethoxypropane (1.06 mL, 8.66 mmol), and para-toluenesulfonic acid monohydrate (0.333 g, 1.73 mmol) were dissolved in acetone (43 mL). The solution was stirred at room temperature overnight and then heated to 40° C. for 3 hours. Once cooled to room temperature, saturated sodium bicarbonate solution was added to the reaction mixture and then approximately half the solvent was removed in vacuo. The resulting solution was diluted with water and extracted four times with CH2Cl2. Combined organics were washed with brine and dried over Na2SO4. The crude material was purified by silica gel chromatography (0 to 5% MeOH/CH2Cl2) to isolate the title compound (0.419 g, 59%)

후처리

  1. temperatureheated to 40° C. for 3 hours
  2. temperatureOnce cooled to room temperature
  3. customapproximately half the solvent was removed in vacuo
  4. additionThe resulting solution was diluted with water
  5. extractionextracted four times with CH2Cl2
  6. washCombined organics were washed with brine
  7. dry with materialdried over Na2SO4
  8. customThe crude material was purified by silica gel chromatography (0 to 5% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-fb48fd8290eb48d1bdd1f3c77947b513
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07951810B2

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