Cyclopentylamine → (2R,3R,4R,5R)-4-acetyloxy-2-(acetyloxymethyl)-5-[6-(cyclopentylamino)-2-iodopurin-9-yl]oxolan-3-yl acetate

HRID 130311

反応式

HRID 130311 の反応式
[C:1]([O:4][CH2:5][C@@H:6]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:8]([N:19]2[CH:27]=[N:26][C:25]3[C:20]2=[N:21][C:22]([I:29])=[N:23][C:24]=3Cl)[O:7]1)(=[O:3])[CH3:2].[CH:30]1([NH2:35])[CH2:34][CH2:33][CH2:32][CH2:31]1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[C:12]([O:11][C@H:10]1[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:8]([N:19]2[CH:27]=[N:26][C:25]3[C:20]2=[N:21][C:22]([I:29])=[N:23][C:24]=3[NH:35][CH:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)[O:7][C@@H:6]1[CH2:5][O:4][C:1](=[O:3])[CH3:2])(=[O:14])[CH3:13]

参加物

5

反応物 3

HCID 2906CyclopentylamineHCID 81531DiisopropylethylamineHCID 482588Acetic acid (2R,3R,4R,5R)-3,4-diacetoxy-5-(6-chloro-2-iodo-purin-9-YL)-tetrahydro-furan-2-ylmethyl ester

生成物 1

HCID 14886862(2R,3R,4R,5R)-4-acetyloxy-2-(acetyloxymethyl)-5-[6-(cyclopentylamino)-2-iodopurin-9-yl]oxolan-3-yl acetate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

1.15 g of [(2R,3R,4R,5R)-3,4-diacetyloxy-5-(6-chloro-2-iodopurin-9-yl)oxolan-2-yl]methyl acetate (Toronto Research Chemicals) was placed in 20 mL of DMF (dimethylformamide) and stirred. To this solution was added 0.42 mL of cyclopentyl amine and 10 mL of DIPEA (diisopropylethylamine). The resulting mixture was stirred overnight at room temperature. The next morning, the solvent was removed and the residue purified using a dichloromethane/methanol 20:1 column to provide (2R,3R,4R,5R)-4-acetyloxy-2-(acetyloxymethyl)-5-[6-(cyclopentylamino)-2-iodopurin-9-yl]oxolan-3-yl acetate, a compound of formula (10).

後処理

  1. stirringThe resulting mixture was stirred overnight at room temperature
  2. customThe next morning, the solvent was removed
  3. customthe residue purified

出典と根拠

ORDレコード
ord-61a9967aeaa54b84a6ad1180b491e204
出典データセット
uspto-grants-2008_06
特許番号
US07381714B2

関連ノート

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