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Triphenylphosphine → (R)-1-(5-acetoxyhexyl)-8-bromo-7-(2-(N-tert-butoxycarbonylamino)ethyl)-3-methylxanthine

HRID 1355406
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HRID 1355406 반응식
[C:1]([O:4][C@H:5]([CH3:23])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[NH:17][C:16]([Br:21])=[N:15][C:14]=2[N:13]([CH3:22])[C:11]1=[O:12])(=[O:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:43]([O:47][C:48]([NH:50][CH2:51][CH2:52]CO)=[O:49])([CH3:46])([CH3:45])[CH3:44].CCOC(/N=N/C(OCC)=O)=O>ClCCCl>[C:1]([O:4][C@H:5]([CH3:23])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[N:17]([CH2:52][CH2:51][NH:50][C:48]([O:47][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:49])[C:16]([Br:21])=[N:15][C:14]=2[N:13]([CH3:22])[C:11]1=[O:12])(=[O:3])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 3838134tert-butyl N-(3-hydroxypropyl)carbamateHCID 5462977Diethyl azodicarboxylateHCID 69154488(R)-1-(5-acetoxyhexyl)-8-bromo-3-methylxanthine

생성물 1

HCID 69154900(R)-1-(5-acetoxyhexyl)-8-bromo-7-(2-(N-tert-butoxycarbonylamino)ethyl)-3-methylxanthine수율 87.1%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

To a stirring suspension of (R)-1-(5-acetoxyhexyl)-8-bromo-3-methylxanthine (5.10 g, 13.2 mmol), triphenylphosphine (5.24 g, 20.0 mmol) and 3-(tert-butoxycarbonylamino)-1-propanol (3.2 g, 20.0 mmol) in anhydrous 1,2-dichloroethane (100 ml) at room temperature was added diethylazodicarboxylate (3.48 g, 20.0 mmol) dropwise. The mixture was stirred at room temperature overnight and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with ethyl acetate-hexane (1:1) to provide (R)-1-(5-acetoxyhexyl)-8-bromo-7-(2-(N-tert-butoxycarbonylamino)ethyl)-3-methylxanthine (6.10 g, 85% yield) as a beige oil.

후처리

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by column chromatography on silica gel eluting with ethyl acetate-hexane (1:1)

출처 및 근거

ORD 기록
ord-6fea98f11c444c23bfb1f67c4d0f61e9
출처 데이터셋
uspto-grants-2003_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06586429B2

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