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Benzoyl chloride → N-{[9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl]methyl}benzamide

HRID 2268342
ノート
印刷プレビュー

反応式

HRID 2268342 の反応式
[NH2:1][CH2:2][C:3]1[N:11]=[C:10]2[C:6]([N:7]=[CH:8][N:9]2[C@H:12]2[C@H:16]([OH:17])[C@H:15]([OH:18])[C@@H:14]([CH2:19][O:20][CH3:21])[O:13]2)=[C:5]([NH:22][CH2:23][CH:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:4]=1.C(N(CC)CC)C.[C:44](Cl)(=[O:51])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>O1CCCC1>[OH:17][C@@H:16]1[C@H:15]([OH:18])[C@@H:14]([CH2:19][O:20][CH3:21])[O:13][C@H:12]1[N:9]1[CH:8]=[N:7][C:6]2[C:10]1=[N:11][C:3]([CH2:2][NH:1][C:44](=[O:51])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[N:4][C:5]=2[NH:22][CH2:23][CH:24]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 9897827(2R,3R,4S,5R)-2-{2-(Aminomethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol

生成物 1

HCID 9808686N-{[9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl]methyl}benzamide収率 67.3%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒
2 回

実験手順

A stirred solution of (2R,3R,4S,5R)-2-{2-(aminomethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol (example 1) (110 mg, 0.22 mmol) in dry tetrahydrofuran (20 ml) was treated with triethylamine (0.1 ml, 0.72 mmol) and the mixture heated gently until all components had dissolved. The solution was then cooled to room temperature, treated with a solution of benzoyl chloride (28 mg, 0.20 mmol) in dry tetrahydrofuran (2 ml) and the mixture stirred for 1.5 hr. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol (95:5), to give the product which was then triturated with a mixture of diethyl ether and pentane, filtered off and dried to afford the title compound as a solid (80 mg). MS: 595 (MH+).

後処理

  1. temperaturethe mixture heated gently until all components
  2. dissolutionhad dissolved
  3. customThe solvent was removed under reduced pressure
  4. customthe residue purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol (95:5)
  5. customto give the product which
  6. customwas then triturated with a mixture of diethyl ether and pentane
  7. filtrationfiltered off
  8. customdried

出典と根拠

ORDレコード
ord-008c54d20da040039e34deeee0b6318f
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

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