Triphenylphosphine → 2-{2-[6-Nitro-7-chloro-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid benzyl ester

HRID 1858064노트

반응식

HRID 1858064 반응식
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[CH2:17][CH2:18][OH:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[Cl:53][C:54]1[CH:63]=[C:62]2[C:57]([C:58](O)=[C:59]([C:65]3[CH:70]=[C:69]([CH3:71])[CH:68]=[C:67]([CH3:72])[CH:66]=3)[C:60](=[O:64])[NH:61]2)=[CH:56][C:55]=1[N+:74]([O-:76])=[O:75]>>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[CH2:17][CH2:18][O:19][C:58]1[C:57]2[C:62](=[CH:63][C:54]([Cl:53])=[C:55]([N+:74]([O-:76])=[O:75])[CH:56]=2)[NH:61][C:60](=[O:64])[C:59]=1[C:65]1[CH:66]=[C:67]([CH3:72])[CH:68]=[C:69]([CH3:71])[CH:70]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 45358666Benzyl 2-(2-hydroxyethyl)piperidine-1-carboxylateHCID 547112387-chloro-3-(3,5-dimethylphenyl)-4-hydroxy-6-nitro-1H-quinolin-2-one

생성물 1

HCID 544370152-{2-[6-Nitro-7-chloro-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid benzyl ester수율 64%

실험 절차

To a solution of 7-chloro-3-(3,5-dimethylphenyl)-4-hydroxy-6-nitro-1H-quinolin-2-one (13.5 g in 600 mL of N,N-dimethylformamide) was added 9.2 g of 2-(2-hydroxyethyl)-piperidine-1-carboxylic acid benzyl ester and 14 g of triphenylphosphine followed by 10.4 mL of diisopropyl azodicarboxylate and the mixture stirred at room temperature. After 24 hours, the solvents were removed in vacuo and the residue resolvated in methylene chloride, washed with water and purified by flash chromatography on silica gel (hexane:ethyl acetate, 90:10; then methylene chloride:ethyl acetate, 95:5) to give the title compound (13.2 g).

후처리

  1. customthe solvents were removed in vacuo
  2. washwashed with water
  3. custompurified by flash chromatography on silica gel (hexane

출처 및 근거

ORD 기록
ord-e5ac50d7bd0b4e8a863f3d0795e26cb7
출처 데이터셋
uspto-grants-2000_11
특허 번호
US06150352

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