Triethylamine → 3-((2s)-3-{2-Ethyl-4-[5-(5-isobutyl-4-methyl-pyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-2-hydroxy-propylamino)-propionic acid methyl ester

HRID 2037380Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2037380
[CH2:1]([C:3]1[CH:15]=[C:14]([C:16]2[N:20]=[C:19]([C:21]3[CH:26]=[C:25]([CH3:27])[C:24]([CH2:28][CH:29]([CH3:31])[CH3:30])=[CH:23][N:22]=3)[O:18][N:17]=2)[CH:13]=[C:12]([CH3:32])[C:4]=1[O:5][CH2:6][C@@H:7]([OH:11])[CH2:8][NH:9][CH3:10])[CH3:2].Cl.[CH3:34][O:35][C:36](=[O:40])[CH2:37]CN.C(N(CC)CC)C>CO>[CH3:34][O:35][C:36](=[O:40])[CH2:37][CH2:10][NH:9][CH2:8][C@H:7]([OH:11])[CH2:6][O:5][C:4]1[C:12]([CH3:32])=[CH:13][C:14]([C:16]2[N:20]=[C:19]([C:21]3[CH:26]=[C:25]([CH3:27])[C:24]([CH2:28][CH:29]([CH3:31])[CH3:30])=[CH:23][N:22]=3)[O:18][N:17]=2)=[CH:15][C:3]=1[CH2:1][CH3:2]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 2734767Methyl 3-aminopropanoate hydrochlorideHCID 68629918(s)-1-{2-Ethyl-4-[5-(5-isobutyl-4-methyl-pyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-3-methylamino-propan-2-ol

Produkt 1

HCID 686312243-((2s)-3-{2-Ethyl-4-[5-(5-isobutyl-4-methyl-pyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-2-hydroxy-propylamino)-propionic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of the epoxide intermediate of Example 57 (step a, 150 mg, 368 μmol), β-alanine methyl ester hydrochloride (113 mg, 736 μmol) and triethylamine (93 mg, 920 μmol) in methanol (5 mL) is stirred at 60° C. for 20 h. The solvent is removed in vacuo and the crude product is purified on prep. TLC plates using DCM:methanol 10:1 to give the title compound (53 mg) as a colourless oil; LC-MS: tR=0.92 min, [M+H]+=511.18.

Aufarbeitung

  1. customThe solvent is removed in vacuo
  2. customthe crude product is purified on prep

Quellen und Nachweise

ORD-Eintrag
ord-ada813ea36264dcd92d44d771c3a3299
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575200B2

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