Sodium hydride → HCID 69563543, compound

HRID 2181229Notes

Reaction equation

HRID 2181229 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH:5]([O:17][CH2:18][CH3:19])[CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[C:10]2[CH3:16])[CH3:2].Cl[CH2:22][C:23]1[N:24]=[C:25]([C:29]2[CH:34]=[CH:33][C:32]([CH:35]([CH3:37])[CH3:36])=[CH:31][CH:30]=2)[O:26][C:27]=1[CH3:28].[H-].[Na+]>CN(C)C=O.O>[CH2:1]([O:3][C:4](=[O:20])[CH:5]([O:17][CH2:18][CH3:19])[CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH2:22][C:23]1[N:24]=[C:25]([C:29]3[CH:30]=[CH:31][C:32]([CH:35]([CH3:37])[CH3:36])=[CH:33][CH:34]=3)[O:26][C:27]=1[CH3:28])[CH:11]=[C:10]2[CH3:16])[CH3:2]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 219742554-(Chloromethyl)-2-(4-isopropylphenyl)-5-methyloxazoleHCID 69563048HCID 69563048, compound

Product 1

HCID 69563543HCID 69563543, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

0.28 g (1.0 mmol) rac-2-ethoxy-3-(3-methyl-1H-indol-5-yl)-propionic acid ethyl ester (preparation 4) and 0.30 g (1.2 mmol) 4-chloromethyl-2-(4-isopropyl-phenyl)-5-methyl-oxazole were dissolved under argon in 5.0 ml N,N-dimethylformamide; 0.048 g (1.1 mmol) sodium hydride (55% in mineral oil) were added and the reaction mixture then stirred for 48 hours at ambient temperature. It was then diluted with water and extracted with ether. The combined organic phases were dried over MgSO4 and evaporated. The residue formed was purified by flash-chromatography (silica gel; eluent: gradient of hexane and ethyl acetate) to give 0.32 g (67%) of rac-2-ethoxy-3-{1-[2-(4-isopropyl-phenyl)-5-methyl-oxazol-4-ylmethyl]-3-methyl-1H-indol-5-yl}-propionic acid ethyl ester as colorless oil.

Workup

  1. extractionextracted with ether
  2. dry with materialThe combined organic phases were dried over MgSO4
  3. customevaporated
  4. customThe residue formed
  5. customwas purified by flash-chromatography (silica gel; eluent: gradient of hexane and ethyl acetate)

Sources & evidence

ORD record
ord-1e727277afd4466abb3480e97c0ba235
Source dataset
uspto-grants-2005_05
Patent number
US06890947B2

Reaction notes

Loading…