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 391963Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 391963
[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.C[O:26][C:27](=[O:78])[C@@H:28]([NH:45][C:46]([C@@H:48]1[CH2:57][C:56]2[CH:55]=[C:54]3[O:58][CH2:59][C@H:60]([C:62]4[CH:67]=[CH:66][C:65]([O:68][CH2:69][C:70]5[CH:75]=[CH:74][C:73]([Cl:76])=[C:72]([Cl:77])[CH:71]=5)=[CH:64][CH:63]=4)[O:61][C:53]3=[CH:52][C:51]=2[CH2:50][NH:49]1)=[O:47])[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][C:37]2[CH:42]=[CH:41][N:40]=[C:39]([CH3:43])[C:38]=2[CH3:44])=[CH:32][CH:31]=1>C(Cl)Cl>[Cl:77][C:72]1[CH:71]=[C:70]([CH:75]=[CH:74][C:73]=1[Cl:76])[CH2:69][O:68][C:65]1[CH:66]=[CH:67][C:62]([C@H:60]2[CH2:59][O:58][C:54]3=[CH:55][C:56]4[CH2:57][C@@H:48]([C:46]([NH:45][C@@H:28]([CH2:29][C:30]5[CH:35]=[CH:34][C:33]([O:36][C:37]6[CH:42]=[CH:41][N:40]=[C:39]([CH3:43])[C:38]=6[CH3:44])=[CH:32][CH:31]=5)[C:27]([OH:78])=[O:26])=[O:47])[N:49]([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)[CH2:50][C:51]=4[CH:52]=[C:53]3[O:61]2)=[CH:63][CH:64]=1

Komponenten

5

Edukt 3

HCID 7121Veratric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 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 EDCI 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-c3c74fd8c2454052bc34998114730cdb
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383644B2

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