1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → benzyl {(5S)-5-{[(5-methoxy-2-methyl-1H-indol-3-yl)acetyl]amino}-5-[5-(2-naphthyl)-1H-imidazol-2-yl]pentyl}carbamate

HRID 659712

Reaktionsgleichung

Reaktionsgleichung von HRID 659712
FC(F)(F)[C:3]([O-:5])=[O:4].F[C:9](F)(F)[C:10]([O-:12])=O.[NH3+:15][C@H:16]([C:32]1[NH:33][C:34]([C:37]2[CH:46]=[CH:45][C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH:38]=2)=[CH:35][NH+:36]=1)[CH2:17][CH2:18][CH2:19][CH2:20][NH:21]C(OCC1C=CC=CC=1)=O.[CH3:47]CN=C=NCCCN(C)C.[CH:58]1[CH:59]=[CH:60][C:61]2N(O)N=N[C:62]=2[CH:63]=1.[CH3:68][O:69][C:70]1[CH:71]=[C:72]2[C:76](=[CH:77][CH:78]=1)[NH:75][C:74]([CH3:79])=[C:73]2CC(O)=O.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[CH3:68][O:69][C:70]1[CH:71]=[C:72]2[C:76](=[CH:77][CH:78]=1)[NH:75][C:74]([CH3:79])=[C:73]2[CH2:9][C:10]([NH:15][C@H:16]([C:32]1[NH:33][C:34]([C:37]2[CH:46]=[CH:45][C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH:38]=2)=[CH:35][N:36]=1)[CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:3](=[O:4])[O:5][CH2:47][C:62]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:63]=1)=[O:12]

Komponenten

8

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 761515-Methoxy-2-methylindole-3-acetic acidHCID 81531DiisopropylethylamineHCID 866315362-((1S)-1-ammonio-5-{[(benzyloxy)carbonyl]amino}pentyl)-5-(2-naphthyl)-1H-imidazol-3-ium bis(trifluoroacetate)

Produkt 1

HCID 86631539benzyl {(5S)-5-{[(5-methoxy-2-methyl-1H-indol-3-yl)acetyl]amino}-5-[5-(2-naphthyl)-1H-imidazol-2-yl]pentyl}carbamateAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution (0.5 M) of the product from step 2 in DMF were added EDCI (1.5 eq.), HOBt (1.5 eq.), (5-methoxy-2-methyl-1H-indol-3-yl)acetic acid (1.5 eq.) and DIPEA (6 eq.) and the reaction mixture was stirred at RT for 16 h. Then, it was diluted with EtOAc and washed with 1N HCl, brine and dried. Evaporation of the solvent under reduced pressure gave a crude that was purified by flash chromatography on silica gel (1:4 to 1:3 EtOAc/petroleum ether) to yield (77%) the title compound as a solid.

Aufarbeitung

  1. washwashed with 1N HCl, brine
  2. customdried
  3. customEvaporation of the solvent under reduced pressure
  4. customgave a crude that
  5. customwas purified by flash chromatography on silica gel (1:4 to 1:3 EtOAc/petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-a6fd1f79528546ada0afbdf313119303
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08080573B2

Verknüpfte Notizen

Wird geladen…