Triethylamine → HCID 131716727, compound

HRID 1110675Notes

Reaction equation

HRID 1110675 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

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 21186548Diazomethane diethyletherHCID 53977897HCID 53977897, compound

Product 1

HCID 131716727HCID 131716727, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

N-[2-{4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy}propionylalanine (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

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

Sources & evidence

ORD record
ord-d23e97e2eaa7447bbf462592432870c7
Source dataset
uspto-grants-1990_12
Patent number
US04976773

Reaction notes

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