Ethylmorpholine → 4-[(R)-2-((S)-2-Cyclobutylcarbamoyl-pyrrolidin-1-yl)-1-methyl-2-oxo-ethoxy]-7-methyl-quinoline-2-carboxylic acid methyl ester

HRID 1185560ノート

反応式

HRID 1185560 の反応式
[C:1]([C@H:4]([O:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([CH3:17])=[CH:14][CH:15]=2)[N:10]=[C:9]([C:18]([OH:20])=[O:19])[CH:8]=1)[CH3:5])([OH:3])=O.F[C:22]1C(O)=C(F)C(F)=C(F)C=1F.Cl.[CH:34]1([NH:38][C:39]([C@@H:41]2[CH2:45][CH2:44][CH2:43][NH:42]2)=[O:40])[CH2:37][CH2:36][CH2:35]1.C(N1CCOCC1)C>C(Cl)Cl.O.C(Cl)CCl>[CH3:22][O:20][C:18]([C:9]1[CH:8]=[C:7]([O:6][C@H:4]([CH3:5])[C:1]([N:42]2[CH2:43][CH2:44][CH2:45][C@H:41]2[C:39](=[O:40])[NH:38][CH:34]2[CH2:37][CH2:36][CH2:35]2)=[O:3])[C:16]2[C:11](=[CH:12][C:13]([CH3:17])=[CH:14][CH:15]=2)[N:10]=1)=[O:19]

参加物

8

反応物 4

HCID 7525EthylmorpholineHCID 13041PentafluorophenolHCID 68597555(S)-Pyrrolidine-2-carboxylic acid cyclobutylamide hydrochlorideHCID 68598842HCID 68598842、化合物

生成物 1

HCID 686020364-[(R)-2-((S)-2-Cyclobutylcarbamoyl-pyrrolidin-1-yl)-1-methyl-2-oxo-ethoxy]-7-methyl-quinoline-2-carboxylic acid methyl ester

試薬・触媒・溶媒 3

HCID 111,2-Dichloroethane溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 1.30 g 4-((R)-1-Carboxy-ethoxy)-7-methyl-quinoline-2-carboxylic acid in 10 ml DCM, 1.24 g pentafluorophenol and 1.29 g EDC were added. The mixture was stirred under exclusion of moisture until LCMS indicated complete conversion to the corresponding pentafluorophenolester. (S)-Pyrrolidine-2-carboxylic acid cyclobutylamide hydrochloride (1.10 g) was mixed with 1.1 ml N-ethylmorpholine and 5 ml DCM and this mixture added dropwise to the solution of the pentafluorophenolester. After 12 h the reaction mixture was diluted with water and extracted with DCM. The crude product obtained after evaporation of the solvent was purified by flash chromatography on silica eluting with ethyl acetate/heptane gradient. Yield: 1.40 g.

後処理

  1. additionthis mixture added dropwise to the solution of the pentafluorophenolester
  2. extractionextracted with DCM

出典と根拠

ORDレコード
ord-41f7b184e12b413188878ca786c33331
出典データセット
uspto-grants-2014_03
特許番号
US08669266B2

反応ノート

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