Sodium hydride → HCID 67072102, compound

HRID 1242386Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:19])[C:5]([CH3:18])([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14](=[O:17])[NH:15][CH3:16])[CH:9]=1)[CH3:6])[CH3:2].[CH3:20][C:21]1[C:26]([CH2:27]OS(C)(=O)=O)=[CH:25][CH:24]=[C:23]([C:33]2[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=2)[N:22]=1.[H-].[Na+]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:19])[C:5]([CH3:18])([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14](=[O:17])[N:15]([CH3:16])[CH2:27][C:26]2[C:21]([CH3:20])=[N:22][C:23]([C:33]3[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=3)=[CH:24][CH:25]=2)[CH:9]=1)[CH3:6])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

0.28 g (1.05 mmol) of 2-methyl-2-(3-methylcarbamoyl-phenoxy)-propionic acid ethyl ester and 0.36 g (1.05 mmol) of methanesulfonic acid 2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-ylmethyl ester (example 59E]) were dissolved in 15 ml of DMF. The reaction mixture was cooled down to 0° C. and 0.05 g (1.20 mmol) of sodium hydride (55% in mineral oil) was added. After stirring for sixteen hours at ambient temperature, the reaction mixture was poured into crashed ice and extracted twice with Et2O. The combined organic phases were washed with water and brine and dried over anhydrous magnesium sulfate. After evaporation of the solvent, the crude product was purified by flash chromatography (SiO2, heptane/EtOAc) to give 0.249 g of the title compound as yellow oil.

Workup

additionthe reaction mixture was poured
extractionextracted twice with Et2O
washThe combined organic phases were washed with water and brine
dry with materialdried over anhydrous magnesium sulfate
customAfter evaporation of the solvent
customthe crude product was purified by flash chromatography (SiO2, heptane/EtOAc)

Sources & evidence

ORD record: ord-8126fad8d42641de96f57702634e1b1f
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115611B2

Reaction notes

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