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

HRID 1185515Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1185515
[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]

Komponenten

8

Edukt 4

HCID 7525EthylmorpholineHCID 13041PentafluorophenolHCID 68597555(S)-Pyrrolidine-2-carboxylic acid cyclobutylamide hydrochlorideHCID 68598842HCID 68598842, Verbindung

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 111,2-DichloroethaneLösungsmittelHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-0edff2d9768c43fa97950788d4b50a9f
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08669266B2

Notizen zur Reaktion

Wird geladen…