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 1858064ノート

反応式

HRID 1858064 の反応式
[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

参加物

5

反応物 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

生成物 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 ester収率 64%

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-e5ac50d7bd0b4e8a863f3d0795e26cb7
出典データセット
uspto-grants-2000_11
特許番号
US06150352

反応ノート

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