Acetic Anhydride → (R)-1-(5-acetoxyhexyl)-8-(2-chloroethylamino)-3-methylxanthine

HRID 1296396ノート

反応式

HRID 1296396 の反応式
[Cl:1][CH2:2][CH2:3][NH:4][C:5]1[NH:13][C:12]2[C:11](=[O:14])[N:10]([CH2:15][CH2:16][CH2:17][CH2:18][C@H:19]([OH:21])[CH3:20])[C:9](=[O:22])[N:8]([CH3:23])[C:7]=2[N:6]=1.C(N(CC)CC)C.[C:31](OC(=O)C)(=[O:33])[CH3:32]>CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl>[C:31]([O:21][C@H:19]([CH3:20])[CH2:18][CH2:17][CH2:16][CH2:15][N:10]1[C:11](=[O:14])[C:12]2[NH:13][C:5]([NH:4][CH2:3][CH2:2][Cl:1])=[N:6][C:7]=2[N:8]([CH3:23])[C:9]1=[O:22])(=[O:33])[CH3:32]

参加物

6

反応物 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 69154242(R)-1-(5-hydroxyhexyl)-8-(2-chloroethylamino)-3-methylxanthine

生成物 1

HCID 69154552(R)-1-(5-acetoxyhexyl)-8-(2-chloroethylamino)-3-methylxanthine収率 89.1%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6212Chloroform溶媒

実験手順

To a stirring mixture of (R)-8-(2-chloroethylamino)-1-(5-hydroxyhexyl)-3-methylxanthine (2.2 g, 6.4 mmol), triethylamine (1.94 g, 19.2 mmol) and 4-dimethylaminopyridine (0.39 g, 3.2 mmol) in chloroform (50 ml) at 0-5° C. was added acetic anhydride (1.30 g, 12.8 mmol). The mixture was warmed to room temperature, stirred overnight, and concentrated under reduced pressure. The residue was purified by column chromatography eluting with ethylacetate-methanol (7:1) to provide (R)-1-(5-acetoxyhexyl)-8-(2-chloroethylamino)-3-methylxanthine (2.2 g, 89% yield) as a white powder.

後処理

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by column chromatography
  3. washeluting with ethylacetate-methanol (7:1)

出典と根拠

ORDレコード
ord-277c249a883c415d872db9d741c0a732
出典データセット
uspto-grants-2007_07
特許番号
US07247630B2

反応ノート

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