Tetrabutylammonium Fluoride → (2R,3R,4S,5R)-2-(6-[(2,2-Diphenylethyl)amino]-2-{2-[(1-ethylpropyl)amino]ethyl}-9H-purin-9-yl)-5-(methoxymethyl)tetrahydro-3,4-furandiol

HRID 2268356ノート

反応式

HRID 2268356 の反応式
[Si]([O:8][C@@H:9]1[C@H:13]([O:14][Si](C(C)(C)C)(C)C)[C@@H:12]([CH2:22][O:23][CH3:24])[O:11][C@H:10]1[N:25]1[CH:33]=[N:32][C:31]2[C:26]1=[N:27][C:28]([CH2:49][CH2:50][NH:51][CH:52]([CH2:55][CH3:56])[CH2:53][CH3:54])=[N:29][C:30]=2[NH:34][CH2:35][CH:36]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[C:37]1([CH:36]([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH2:35][NH:34][C:30]2[N:29]=[C:28]([CH2:49][CH2:50][NH:51][CH:52]([CH2:53][CH3:54])[CH2:55][CH3:56])[N:27]=[C:26]3[C:31]=2[N:32]=[CH:33][N:25]3[C@H:10]2[C@H:9]([OH:8])[C@H:13]([OH:14])[C@@H:12]([CH2:22][O:23][CH3:24])[O:11]2)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

参加物

5

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 69534102N-(2-{9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}ethyl)-N-(1-ethylpropyl)amine

生成物 1

HCID 9872937(2R,3R,4S,5R)-2-(6-[(2,2-Diphenylethyl)amino]-2-{2-[(1-ethylpropyl)amino]ethyl}-9H-purin-9-yl)-5-(methoxymethyl)tetrahydro-3,4-furandiol収率 56.1%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

N-(2-{9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}ethyl)-N-(1-ethylpropyl)amine (250 mg, 0.31 mmol) (preparation 19) was dissolved in dry tetrahydrofuran (1 ml), a 1M solution of tetra-n-butylammonium fluoride in tetrahydrofuran (1 ml, 1 mmol) added and the mixture stirred at room temperature for 3 days. The solvent was removed under reduced pressure and the residue purified by column chromatography eluting with a gradient system of dichloromethane:methanol:ammonia (94:6:0.6) changing to dichloromethane:methanol:ammonia (90:10:1) to give the crude product as a foam. This was dissolved in ethyl acetate (15 ml) and the solution washed sequentially with dilute aqueous sodium hydroxide solution, brine and water, then dried with anhydrous sodium sulfate. The solvent removed under reduced pressure to give the title compound as a powder (100 mg). MS: 575 (MH+)

後処理

  1. customThe solvent was removed under reduced pressure
  2. customthe residue purified by column chromatography
  3. washeluting with a gradient system of dichloromethane:methanol:ammonia (94:6:0.6)
  4. customto give the crude product as a foam
  5. washthe solution washed sequentially with dilute aqueous sodium hydroxide solution, brine and water
  6. dry with materialdried with anhydrous sodium sulfate
  7. customThe solvent removed under reduced pressure

出典と根拠

ORDレコード
ord-26f0047df44a4639a3775fcc94b8c7da
出典データセット
uspto-grants-2001_12
特許番号
US06326359B1

反応ノート

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