1,2-Dichloroethane → 4-[(S)-4-tert-Butoxycarbonyl-2-({4-[(R)-2-((S)-2-cyclobutylcarbamoyl-pyrrolidin-1-yl)-1-methyl-2-oxo-ethoxy]-7-methyl-quinoline-2-carbonyl}-amino)-butyryl]-piperazine-1-carboxylic acid ethyl ester

HRID 1185453Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1185453
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:43])[C@@H:13]([NH:23][C:24]([C:26]2[CH:35]=[C:34]([O:36][C@@H:37]([C:39]([OH:41])=O)[CH3:38])[C:33]3[C:28](=[CH:29][C:30]([CH3:42])=[CH:31][CH:32]=3)[N:27]=2)=[O:25])[CH2:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:8][CH2:7]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:67]1([NH:71][C:72]([C@@H:74]2[CH2:78][CH2:77][CH2:76][NH:75]2)=[O:73])[CH2:70][CH2:69][CH2:68]1>C(Cl)Cl.O>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:43])[C@@H:13]([NH:23][C:24]([C:26]2[CH:35]=[C:34]([O:36][C@H:37]([CH3:38])[C:39]([N:75]3[CH2:76][CH2:77][CH2:78][C@H:74]3[C:72](=[O:73])[NH:71][CH:67]3[CH2:68][CH2:69][CH2:70]3)=[O:41])[C:33]3[C:28](=[CH:29][C:30]([CH3:42])=[CH:31][CH:32]=3)[N:27]=2)=[O:25])[CH2:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Komponenten

7

Edukt 4

HCID 111,2-DichloroethaneHCID 13041PentafluorophenolHCID 685972714-((S)-4-tert-Butoxycarbonyl-2-{[4-((R)-1-carboxy-ethoxy)-7-methyl-quinoline-2-carbonyl]-amino}-butyryl)-piperazine-1-carboxylic acid ethyl esterHCID 68599196(S)-Pyrrolidine-2-carboxylic acid cyclobutylamide trifluoroacetate

Produkt 1

HCID 686019374-[(S)-4-tert-Butoxycarbonyl-2-({4-[(R)-2-((S)-2-cyclobutylcarbamoyl-pyrrolidin-1-yl)-1-methyl-2-oxo-ethoxy]-7-methyl-quinoline-2-carbonyl}-amino)-butyryl]-piperazine-1-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 250 mg of 4-((S)-4-tert-Butoxycarbonyl-2-{[4-((R)-1-carboxy-ethoxy)-7-methyl-quinoline-2-carbonyl]-amino}-butyryl)-piperazine-1-carboxylic acid ethyl ester in 2.5 ml of DCM, 96 mg of EDC, 92 mg of pentafluorophenol was added and the reaction mixture was stirred for 2 h. Then, 117 mg of (S)-Pyrrolidine-2-carboxylic acid cyclobutylamide trifluoroacetate and 192 mg of NEM in 2 ml of DCM was added. After 2 h the reaction mixture was diluted with water. After filtration through a chem Elut® cartridge by eluting with ethyl acetate the solvents were removed under reduced pressure. The isolated crude product was pure enough for the next reaction step.

Aufarbeitung

  1. filtrationAfter filtration through a chem Elut® cartridge
  2. washby eluting with ethyl acetate the solvents
  3. customwere removed under reduced pressure
  4. customThe isolated crude product
  5. customwas pure enough for the next reaction step

Quellen und Nachweise

ORD-Eintrag
ord-36afdfcc0d8445e1948b3e3fffda0fef
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08669266B2

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