Triethylamine → HCID 131716727, compound

HRID 1591017Notes

Reaction equation

[Cl:1][C:2]1[C:3]([O:12][C:13]2[CH:29]=[CH:28][C:16]([O:17][CH:18]([CH3:27])[C:19]([NH:21][C@H:22]([C:24]([OH:26])=[O:25])[CH3:23])=[O:20])=[CH:15][CH:14]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.C(N(CC)CC)C.C([Cl:42])(=O)OCC.[N+](=C)=[N-].CC[O:48][CH2:49][CH3:50]>O1CCCC1.Cl>[Cl:1][CH2:2][C:49]([CH2:50][Cl:42])=[O:48].[Cl:1][C:2]1[C:3]([O:12][C:13]2[CH:14]=[CH:15][C:16]([O:17][CH:18]([CH3:27])[C:19]([NH:21][C@H:22]([C:24]([OH:26])=[O:25])[CH3:23])=[O:20])=[CH:28][CH:29]=2)=[N:4][CH:5]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

N-[2-{4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy}propionyl]alanine (400 mg) was dissolved in 10 ml of tetrahydrofuran, added with 0.15 ml of triethylamine and cooled to 0° C. Ethyl chlorocarbonate (0.1 ml) was added and after 5 minutes, excessive diazomethane ether solution was added, and the mixture was stirred for one hour. Then, several drops of conc. hydrochloric acid were added and, after stirring for 10 minutes, the reaction mixture was washed with water, extracted with ether, and the extract dried over anhydrous magnesium sulfate. The oily product obtained by evaporation of the solvent under a reduced pressure was subjected to silica gel medium pressure column chromatography to obtain 300 mg of the title compound as a colorless oily product.

Workup

stirringafter stirring for 10 minutes
washthe reaction mixture was washed with water
extractionextracted with ether
dry with materialthe extract dried over anhydrous magnesium sulfate
customThe oily product obtained by evaporation of the solvent under a reduced pressure

Sources & evidence

ORD record: ord-8120aa69569c402c86b6fe181265618b
Source dataset: uspto-grants-1993_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05205855

Reaction notes

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