Triethylamine → HCID 86711945, compound

HRID 1475253Notes

Reaction equation

HRID 1475253 reaction equation
Cl.[NH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]([F:16])([F:15])[F:14])=[CH:8][CH:7]=1)=[O:5].Cl[C:18](=[O:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20].CCN(CC)CC>C(Cl)Cl.O>[O:24]=[C:18]([NH:2][CH2:3][C:4](=[O:5])[C:6]1[CH:7]=[CH:8][C:9]([O:12][C:13]([F:14])([F:15])[F:16])=[CH:10][CH:11]=1)[C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 20884Ethoxalyl chlorideHCID 66754828HCID 66754828, compound

Product 1

HCID 86711945HCID 86711945, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-amino-1-(4-(trifluoromethoxy)phenyl)ethanone hydrochloride (9.5 g, 37 mmol) in DCM (150 mL) at 0° C. was added dropwise ethyl 2-chloro-2-oxoacetate (5.6 g, 41 mmol), followed by Et3N (16 mL, 111 mmol). The mixture was stirred at RT for 16 h and then diluted with H2O (200 mL) and extracted with EtOAc (4×80 mL). The combined organic layers were washed with brine (50 mL), dried over Na2SO4, filtered and concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (Petroleum ether:EtOAc=5:1 to 1:1) to give the title compound as a yellow solid (7.8 g, 66%). MS (ES+) C13H12F3NO5 requires: 319. found: 320 [M+H]+.

Workup

  1. extractionextracted with EtOAc (4×80 mL)
  2. washThe combined organic layers were washed with brine (50 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (Petroleum ether:EtOAc=5:1 to 1:1)

Sources & evidence

ORD record
ord-a8b3fb5619e842848e528325d35626d2
Source dataset
uspto-grants-2015_04
Patent number
US09018380B2

Reaction notes

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