Ethyl 3-(methylamino)propanoate → (S)-3-((3-(4-(5-(2-Cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazol-3-yl)-2-ethyl-6-methylphenoxy)-2-hydroxypropyl)(methyl)amino)propanoic acid

HRID 2278802Notes

Reaction equation

[CH:1]1([C:6]2[CH:11]=[C:10]([C:12]3[O:16][N:15]=[C:14]([C:17]4[CH:22]=[C:21]([CH3:23])[C:20]([O:24][CH2:25][C@@H:26]5[CH2:28][O:27]5)=[C:19]([CH2:29][CH3:30])[CH:18]=4)[N:13]=3)[CH:9]=[C:8]([O:31][CH3:32])[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C([O:35][C:36](=[O:41])[CH2:37][CH2:38][NH:39][CH3:40])C>>[CH:1]1([C:6]2[CH:11]=[C:10]([C:12]3[O:16][N:15]=[C:14]([C:17]4[CH:22]=[C:21]([CH3:23])[C:20]([O:24][CH2:25][C@@H:26]([OH:27])[CH2:28][N:39]([CH3:40])[CH2:38][CH2:37][C:36]([OH:41])=[O:35])=[C:19]([CH2:29][CH3:30])[CH:18]=4)[N:13]=3)[CH:9]=[C:8]([O:31][CH3:32])[N:7]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

Reactant 2

HCID 541480Ethyl 3-(methylamino)propanoate

HCID 86702019(S)-5-(2-cyclopentyl-6-methoxypyridin-4-yl)-3-(3-ethyl-5-methyl-4-(oxiran-2-ylmethoxy)phenyl)-1,2,4-oxadiazole

Product 1

HCID 57525018(S)-3-((3-(4-(5-(2-Cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazol-3-yl)-2-ethyl-6-methylphenoxy)-2-hydroxypropyl)(methyl)amino)propanoic acid

Procedure

The title compound is prepared starting from (S)-5-(2-cyclopentyl-6-methoxypyridin-4-yl)-3-(3-ethyl-5-methyl-4-(oxiran-2-ylmethoxy)phenyl)-1,2,4-oxadiazole and ethyl-3-(methylamino)-propanoate in analogy to Example 9; LC-MS: tR=0.95 min, [M+H]+=539.53; 1H NMR (CDCl3): δ 7.84 (s, 1H), 7.82 (s, 1H), 7.48 (s, 1H), 7.27 (s, 1H), 6.49 (s br, 2H), 4.52-4.60 (m, 1H), 4.00 (s, 3H), 3.90-3.96 (m, 1H), 3.84-3.90 (m, 1H), 3.41-3.51 (m, 2H), 3.18-3.39 (m, 3H), 2.97 (s, 3H), 2.68-2.80 (m, 4H), 2.36 (s, 3H), 2.04-2.14 (m, 2H), 1.82-1.94 (m, 4H), 1.68-1.78 (m, 2H), 1.30 (t, J=7.5 Hz, 3H).

Sources & evidence

ORD record: ord-7864e178b40d4a2bac8ae4c75b4e958d
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133179B2

Reaction notes

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