Sodium hydride → Rac-2-ethoxy-3-{1-[3-(5-methyl-2-phenyl-oxazol-4-yl)-propyl]-1h-indol-4-yl}-propionic acid ethyl ester

HRID 11385Notes

Reaction equation

HRID 11385 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH:5]([O:16][CH2:17][CH3:18])[CH2:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][NH:11]2)[CH3:2].[CH3:20][C:21]1[O:25][C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:23][C:22]=1[CH2:32][CH2:33][CH2:34]OS(C)(=O)=O.[H-].[Na+]>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:19])[CH:5]([O:16][CH2:17][CH3:18])[CH2:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][N:11]2[CH2:34][CH2:33][CH2:32][C:22]1[N:23]=[C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[O:25][C:21]=1[CH3:20])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 220878333-(5-Methyl-2-phenyl-1,3-oxazol-4-yl)propyl methanesulfonateHCID 69279879Rac-2-ethoxy-3-(1h-indol-4-yl)-propionic acid ethyl ester

Product 1

HCID 69279850Rac-2-ethoxy-3-{1-[3-(5-methyl-2-phenyl-oxazol-4-yl)-propyl]-1h-indol-4-yl}-propionic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In analogy to the procedures described in examples 1 a] and 1 b], rac-2-ethoxy-3-(1H-indol-4-yl)-propionic acid ethyl ester was reacted with methanesulfonic acid 3-(5-methyl-2-phenyl-oxazol-4-yl)-propyl ester in N,N-dimethylformamide in the presence of sodium hydride to yield rac-2-ethoxy-3-{1-[3-(5-methyl-2-phenyl-oxazol-4-yl)-propyl]-1H-indol-4-yl}-propionic acid ethyl ester, which was subsequently saponified to yield rac-2-ethoxy-3-{1-[3-(5-methyl-2-phenyl-oxazol-4-yl)-propyl]-1H-indol-4-yl}-propionic acid as light brown oil.

Sources & evidence

ORD record
ord-a481b5cc2a034aed9fac6e601a0a3d36
Source dataset
uspto-grants-2006_08
Patent number
US07098228B2

Reaction notes

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