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Triphenylphosphine → {1-[2-(4-Benzyloxy-6-methoxy-[1,5]naphthyridin-3-yloxy)-ethyl]-piperidin-4-yl}-carbamic acid tert-butyl ester

HRID 1019993
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HRID 1019993 반응식
N(C(OCC)=O)=NC(OCC)=O.[CH2:13]([O:20][C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([O:31][CH3:32])[N:29]=2)[N:24]=[CH:23][C:22]=1[OH:33])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[C:34]([O:38][C:39](=[O:50])[NH:40][CH:41]1[CH2:46][CH2:45][N:44]([CH2:47][CH2:48]O)[CH2:43][CH2:42]1)([CH3:37])([CH3:36])[CH3:35].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.CO.C(OCC)(=O)C>[C:34]([O:38][C:39](=[O:50])[NH:40][CH:41]1[CH2:46][CH2:45][N:44]([CH2:47][CH2:48][O:33][C:22]2[CH:23]=[N:24][C:25]3[C:30]([C:21]=2[O:20][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)[CH2:43][CH2:42]1)([CH3:37])([CH3:36])[CH3:35]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 45076484[1-(2-Hydroxy-ethyl)-piperidin-4-yl]-carbamic acid tert-butyl esterHCID 1363794134-Benzyloxy-6-methoxy-[1,5]naphthyridin-3-ol

생성물 1

HCID 66746573{1-[2-(4-Benzyloxy-6-methoxy-[1,5]naphthyridin-3-yloxy)-ethyl]-piperidin-4-yl}-carbamic acid tert-butyl ester수율 116.4%

시약·촉매·용매 3

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

Diethyl azodicarboxylate (5.48 g, 31.46 mmol, 2.0 eq) is added at room temperature to a stirred solution of 4-benzyloxy-6-methoxy-[1,5]naphthyridin-3-ol (4.44 g, 15.73 mmol, 1.0 eq), [1-(2-hydroxy-ethyl)-piperidin-4-yl]-carbamic acid tert-butyl ester (5.76 g, 23.59 mmol, 1.5 eq) and triphenylphosphine (8.25 g, 31.46 mmol, 2.0 eq) in tetrahydrofuran (150 mL). After 15 hours stirring at room temperature, tetrahydrofuran is evaporated and the resulting crude product is purified by column chromatography (silica gel, eluent: ethyl acetate:methanol, 10:0 to 9:1, v/v) to afford {1-[2-(4-benzyloxy-6-methoxy-[1,5]naphthyridin-3-yloxy)-ethyl]-piperidin-4-yl}-carbamic acid tert-butyl ester as a light brown viscous oil (9.31 g, 88% yield).

후처리

  1. customtetrahydrofuran is evaporated
  2. customthe resulting crude product is purified by column chromatography (silica gel, eluent

출처 및 근거

ORD 기록
ord-e8a5248067754cc2bd61f4a17eeabcad
출처 데이터셋
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08716280B2

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