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Water → N-(9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-2-{[2-(1-piperidinyl)ethoxy]methyl}-9H-purin-6-yl)-N-(2,2-diphenylethyl)amine

HRID 2268419
ノート
印刷プレビュー

反応式

HRID 2268419 の反応式
[H-].[Na+].CS([O:7][CH2:8][C:9]1[N:17]=[C:16]2[C:12]([N:13]=[CH:14][N:15]2[C@H:18]2[C@H:22]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[C@H:21]([O:31][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])[C@@H:20]([CH2:39][O:40][CH3:41])[O:19]2)=[C:11]([NH:42][CH2:43][CH:44]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[N:10]=1)(=O)=O.[N:57]1([CH2:63][CH2:64]O)[CH2:62][CH2:61][CH2:60][CH2:59][CH2:58]1.O>O1CCCC1>[Si:24]([O:23][C@@H:22]1[C@H:21]([O:31][Si:32]([C:35]([CH3:38])([CH3:36])[CH3:37])([CH3:33])[CH3:34])[C@@H:20]([CH2:39][O:40][CH3:41])[O:19][C@H:18]1[N:15]1[CH:14]=[N:13][C:12]2[C:16]1=[N:17][C:9]([CH2:8][O:7][CH2:64][CH2:63][N:57]1[CH2:62][CH2:61][CH2:60][CH2:59][CH2:58]1)=[N:10][C:11]=2[NH:42][CH2:43][CH:44]([C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)([C:27]([CH3:29])([CH3:30])[CH3:28])([CH3:25])[CH3:26]
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 962WaterHCID 18232N-PiperidinoethanolHCID 24758Sodium hydrideHCID 86757641{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}methyl methanesulfonate

生成物 1

HCID 69534113
N-(9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-2-{[2-(1-piperidinyl)ethoxy]methyl}-9H-purin-6-yl)-N-(2,2-diphenylethyl)amine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Sodium hydride (24 mg of an 80% dispersion in mineral oil, 0.81 mmol) was added to a stirred solution of {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}methyl methanesulfonate (500 mg, 0.63 mmol) (preparation 16) and 2-(1-piperidinyl)-1-ethanol) (105 mg, 0.81 mmol) in tetrahydrofuran (5 ml). The reaction mixture was stirred for 24 hr at room temperature and then heated at reflux for a further 8 hr. The reaction mixture was then poured into cold water and extracted with ethyl acetate. The organic phase was separated, washed with brine and dried with anhydrous sodium sulfate. The solvent was then removed under reduced pressure to give a residue which was purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol (95:5) to give the title compound (101 mg) as an oil. MS: 833 (MH+).

後処理

  1. temperatureheated
  2. temperatureat reflux for a further 8 hr
  3. extractionextracted with ethyl acetate
  4. customThe organic phase was separated
  5. washwashed with brine
  6. dry with materialdried with anhydrous sodium sulfate
  7. customThe solvent was then removed under reduced pressure
  8. customto give a residue which
  9. customwas purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol (95:5)

出典と根拠

ORDレコード
ord-f97996a9320b42f28ea3d22c9c3cf446
出典データセット
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06326359B1

反応ノート

読み込み中…

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