Reaktionsgleichung
[CH2:1]([O:3][C:4]1[CH:25]=[CH:24][CH:23]=[CH:22][C:5]=1[O:6][C@@H:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]2[N:18]=[CH:17][C:16]([C:19](O)=[O:20])=[CH:15][N:14]=2)[CH2:8]1)[CH3:2].Cl.NC[C:29]1[CH:30]=[C:31]([CH:35]([CH3:41])[C:36]([O:38]CC)=[O:37])[CH:32]=[CH:33][CH:34]=1.C[CH2:43][N:44]=C=NCCCN(C)C.Cl.[Li+].[OH-]>>[CH2:1]([O:3][C:4]1[CH:25]=[CH:24][CH:23]=[CH:22][C:5]=1[O:6][C@@H:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]2[N:14]=[CH:15][C:16]([C:19]([NH:44][CH2:43][C:34]3[CH:29]=[CH:30][C:31]([CH:35]([CH3:41])[C:36]([OH:38])=[O:37])=[CH:32][CH:33]=3)=[O:20])=[CH:17][N:18]=2)[CH2:8]1)[CH3:2]Komponenten
Edukt 4
Produkt 1
Versuchsvorschrift
2-(4-((2-((R)-3-(2-ethoxyphenoxy)piperidin-1-yl)pyrimidine-5-carboxamido)methyl)phenyl)propanoic acid was prepared from (R)-2-(3-(2-ethoxyphenoxy)piperidin-1-yl)pyrimidine-5-carboxylic acid and ethyl 2-(3-(aminomethyl)phenyl)propanoate hydrochloride using Amidation Method 2 (EDCl) and Ester Hydrolysis Method 1 (LiOH). 2-(4-((2-((R)-3-(2-Ethoxyphenoxy)piperidin-1-yl)pyrimidine-5-carboxamido)methyl)phenyl)propanoic acid was isolated by chiral SFC purification: Chiralcel-OJ-H, 5μ, 1.0×25 cm, MeOH/CO2 (20/80), T=35° C.; retention time, Example 15 diasteromer 7.056 min, other diastereomer 7.773 min. 1H NMR (500 MHz, DMSO-d6) δ 12.25 (br s, 1H), 8.84 (app t, 1H), 8.76 (s, 2H), 7.25 (m, 4H), 7.04 (m, 1H), 6.90 (m, 3H), 4.43 (d, 2H), 4.31 (m, 1H), 4.19 (dd, 1H), 3.91 (m, 4H), 3.78 (m, 1H), 3.65 (q, 1H), 2.02 (m, 1H), 1.84 (m, 2H), 1.52 (m, 1H), 1.35 (d, 3H), 1.22 (t, 3H). MS (ES+) 505.2 (M+H).
Quellen und Nachweise
- ORD-Eintrag
- ord-ce3fafbaa29b4077a4689b92dcbfa871
- Quelldatensatz
- uspto-grants-2016_09
- Patentnummer
- US09440949B2
Verknüpfte Notizen
Wird geladen…