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

HRID 1185487ノート

反応式

HRID 1185487 の反応式
[CH2:1]([O:3][C:4]([C:6]1[CH:15]=[C:14]([O:16][CH2:17][C:18]([OH:20])=O)[C:13]2[C:8](=[CH:9][C:10]([CH3:21])=[CH:11][CH:12]=2)[N:7]=1)=[O:5])[CH3:2].C(Cl)CCl.FC1C(O)=C(F)C(F)=C(F)C=1F.FC(F)(F)C(O)=O.[CH:45]1([NH:49][C:50]([C@@H:52]2[CH2:56][CH2:55][CH2:54][NH:53]2)=[O:51])[CH2:48][CH2:47][CH2:46]1>C(Cl)Cl.O>[CH2:1]([O:3][C:4]([C:6]1[CH:15]=[C:14]([O:16][CH2:17][C:18]([N:53]2[CH2:54][CH2:55][CH2:56][C@H:52]2[C:50](=[O:51])[NH:49][CH:45]2[CH2:46][CH2:47][CH2:48]2)=[O:20])[C:13]2[C:8](=[CH:9][C:10]([CH3:21])=[CH:11][CH:12]=2)[N:7]=1)=[O:5])[CH3:2]

参加物

7

反応物 4

HCID 111,2-DichloroethaneHCID 13041PentafluorophenolHCID 68599196(S)-Pyrrolidine-2-carboxylic acid cyclobutylamide trifluoroacetateHCID 686015834-Carboxymethoxy-7-methyl-quinoline-2-carboxylic acid ethyl ester

生成物 1

HCID 685994424-[2-((S)-2-Cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-7-methyl-quinoline-2-carboxylic acid ethyl ester

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 2 g of 4-Carboxymethoxy-7-methyl-quinoline-2-carboxylic acid ethyl ester in 30 ml of DCM, 3.6 g of EDC, 3.4 g of pentafluorophenol, 2.2 g of NEM was added and the reaction mixture was stirred at RT for 2 h. Then, 5.3 g of (S)-Pyrrolidine-2-carboxylic acid cyclobutylamide trifluoroacetate and 2.1 g of NEM in 10 ml of DCM was added. After 16 h the reaction mixture was diluted with water and extracted with DCM (3×150 ml). The combined organic phases were dried over MgSO4 and the solvents were removed under reduced pressure. The crude product was purified by chromatography on silica gel eluting with a gradient of n-heptane/ethyl acetate. The fractions containing the product were combined and the solvent evaporated under reduced pressure. Yield: 2.5 g.

後処理

  1. extractionextracted with DCM (3×150 ml)
  2. dry with materialThe combined organic phases were dried over MgSO4
  3. customthe solvents were removed under reduced pressure
  4. customThe crude product was purified by chromatography on silica gel eluting with a gradient of n-heptane/ethyl acetate
  5. additionThe fractions containing the product
  6. customthe solvent evaporated under reduced pressure

出典と根拠

ORDレコード
ord-19ca049e7ebb4b1f8d352e89e599719b
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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