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

HRID 552719
ノート
印刷プレビュー

反応式

HRID 552719 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180
Acetone
溶媒

実験手順

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%)

後処理

  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)

出典と根拠

ORDレコード
ord-fb48fd8290eb48d1bdd1f3c77947b513
出典データセット
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07951810B2

反応ノート

読み込み中…

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