Icosapent → (2S,3R)-methyl 3-((S)-2-((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenamido)propanoyloxy)-2-(nicotinamido)butanoate

HRID 922087

Reaktionsgleichung

Reaktionsgleichung von HRID 922087
[C:1]([NH:24][C@@H:25]([CH3:45])[C:26]([O:28][C@H:29]([CH3:44])[C@H:30]([NH:35][C:36](=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[N:39][CH:38]=1)[C:31]([O:33][CH3:34])=[O:32])=[O:27])(=[O:23])[CH2:2][CH2:3]/[CH:4]=[CH:5]\[CH2:6]/[CH:7]=[CH:8]\[CH2:9]/[CH:10]=[CH:11]\[CH2:12]/[CH:13]=[CH:14]\[CH2:15]/[CH:16]=[CH:17]\[CH2:18]/[CH:19]=[CH:20]\CC.C(O)(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC>>[C:1]([NH:24][C@@H:25]([CH3:45])[C:26]([O:28][C@H:29]([CH3:44])[C@H:30]([NH:35][C:36](=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[N:39][CH:38]=1)[C:31]([O:33][CH3:34])=[O:32])=[O:27])(=[O:23])[CH2:2][CH2:3][CH2:4]/[CH:5]=[CH:6]\[CH2:7]/[CH:8]=[CH:9]\[CH2:10]/[CH:11]=[CH:12]\[CH2:13]/[CH:14]=[CH:15]\[CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH3:20]

Komponenten

3

Edukt 2

HCID 446284IcosapentHCID 58173182(2S,3R)-methyl 3-((S)-2-((4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamido)propanoyloxy)-2-(nicotinamido)butanoate

Produkt 1

HCID 58173168(2S,3R)-methyl 3-((S)-2-((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenamido)propanoyloxy)-2-(nicotinamido)butanoate

Versuchsvorschrift

The same synthetic sequence outlined above for the preparation of (2S,3R)-methyl 3-((S)-2-((4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamido)propanoyloxy)-2-(nicotinamido)butanoate was used, except that (5Z,8Z,11Z,14Z,17Z)-eicosa-5,8,11,14,17-pentaenoic acid (EPA) was used instead of DHA. MS calculated for C34H47N3O6: 593.35. found: [M+H]+ 594.

Quellen und Nachweise

ORD-Eintrag
ord-ba734e006ff34a7895a189c23e16f5bb
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09278136B2

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