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

HRID 1355388노트

반응식

HRID 1355388 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6212Chloroform용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-83cfed07d84b4bb686c1d2280c026b61
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06586429B2

반응 노트

불러오는 중…