Veratric Acid → (S)-2-{[(3S,8S)-3-[4-(3,4-Dichloro-benzyloxy)-phenyl]-7-(3,4-dimethoxy-benzoyl)-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline-8-carbonyl]-amino}-3-[4-(2,3-dimethyl-pyridin-4-yloxy)-phenyl]-propionic acid

HRID 708752Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 708752
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6]([OH:8])=O.CCN=C=NCCCN(C)C.Cl.C[O:27][C:28](=[O:79])[C@@H:29]([NH:46][C:47]([C@@H:49]1[CH2:58][C:57]2[CH:56]=[C:55]3[O:59][CH2:60][C@H:61]([C:63]4[CH:68]=[CH:67][C:66]([O:69][CH2:70][C:71]5[CH:76]=[CH:75][C:74]([Cl:77])=[C:73]([Cl:78])[CH:72]=5)=[CH:65][CH:64]=4)[O:62][C:54]3=[CH:53][C:52]=2[CH2:51][NH:50]1)=[O:48])[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([O:37][C:38]2[CH:43]=[CH:42][N:41]=[C:40]([CH3:44])[C:39]=2[CH3:45])=[CH:33][CH:32]=1>C(Cl)Cl>[Cl:78][C:73]1[CH:72]=[C:71]([CH:76]=[CH:75][C:74]=1[Cl:77])[CH2:70][O:69][C:66]1[CH:67]=[CH:68][C:63]([C@H:61]2[CH2:60][O:59][C:55]3=[CH:56][C:57]4[CH2:58][C@@H:49]([C:47]([NH:46][C@@H:29]([CH2:30][C:31]5[CH:36]=[CH:35][C:34]([O:37][C:38]6[CH:43]=[CH:42][N:41]=[C:40]([CH3:44])[C:39]=6[CH3:45])=[CH:33][CH:32]=5)[C:28]([OH:79])=[O:27])=[O:48])[N:50]([C:6](=[O:8])[C:5]5[CH:9]=[CH:10][C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=5)[CH2:51][C:52]=4[CH:53]=[C:54]3[O:62]2)=[CH:64][CH:65]=1

Komponenten

5

Edukt 3

HCID 7121Veratric AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58327121(S)-2-({(3S,8S)-3-[4-(3,4-dichloro-benzyloxy)-phenyl]-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline-8-carbonyl}-amino)-3-[4-(2,3-dimethyl-pyridin-4-yloxy)-phenyl]-propionic acid methyl ester

Produkt 1

HCID 58327502(S)-2-{[(3S,8S)-3-[4-(3,4-Dichloro-benzyloxy)-phenyl]-7-(3,4-dimethoxy-benzoyl)-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline-8-carbonyl]-amino}-3-[4-(2,3-dimethyl-pyridin-4-yloxy)-phenyl]-propionic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

3,4-Dimethoxybenzoic acid (1 eq.) was stirred in dry DCM with 0.5 eq EDCl at RT for 1 h. (S)-2-({(3S,8S)-3-[4-(3,4-dichloro-benzyloxy)-phenyl]-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline-8-carbonyl}-amino)-3-[4-(2,3-dimethyl-pyridin-4-yloxy)-phenyl]-propionic acid methyl ester in dry DCM (10 eq benzoic acid relative to amine) was added and the resulting mixture stirred 16 h, then directly purified by flash chromatography. The resulting compound was hydrolyzed according to General Procedure B to give the title compound (5 mg). LCMS (m/z) 919.

Aufarbeitung

  1. additionwas added
  2. customdirectly purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-87ed151041914e81939cc5242a7d4663
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09175003B2

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