Ethyl 3-chloro-3-oxopropionate → ethyl 3-((2-acetyl-5-(trifluoromethyl)phenyl)(tetrahydro-2H-pyran-4-yl)amino)-3-oxopropanoate

HRID 242037Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][C:9]=2[C:18](=[O:20])[CH3:19])[CH2:3][CH2:2]1.Cl[C:22](=[O:29])[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]>C1C=CC=CC=1.C(OCC)(=O)C>[C:18]([C:9]1[CH:10]=[CH:11][C:12]([C:14]([F:15])([F:17])[F:16])=[CH:13][C:8]=1[N:7]([CH:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)[C:22](=[O:29])[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])(=[O:20])[CH3:19]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of 400 mg (1.39 mmol) 1-(2-(tetrahydro-2H-pyran-4-ylamino)-4-(trifluoromethyl)phenyl)ethanone in benzene (5 ml) was added 360 μl (2.78 mmol) ethyl 3-chloro-3-oxopropanoate at 0° C. The reaction mixture was stirred at 80° C. for 4 h. Then the mixture was diluted with ethyl acetate (20 ml) and washed with water (20 ml), brine (20 ml), a sat. aq. Na2CO3 sol. (2×30 ml), dried over anhydrous Na2SO4 and concentrated in vacuo to yield 550 mg (1.37 mmol, 98%) ethyl 3-((2-acetyl-5-(trifluoromethyl)phenyl)(tetrahydro-2H-pyran-4-yl)amino)-3-oxopropanoate, which was used in the next step without further purification.

Workup

washwashed with water (20 ml), brine (20 ml)
dry with materiala sat. aq. Na2CO3 sol. (2×30 ml), dried over anhydrous Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-98bd98bb95f945f9857e2157326b5cc1
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653102B2

Reaction notes

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