Ethoxalyl chloride → Ethyl oxo{[4-(trifluoromethyl)benzyl][4-(3-undecyl-1,2,4-oxadiazol-5-yl)benzyl]amino}acetate

HRID 735832Notes

Reaction equation

Cl.[F:2][C:3]([F:36])([F:35])[C:4]1[CH:34]=[CH:33][C:7]([CH2:8][NH:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[O:21][N:20]=[C:19]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[N:18]=3)=[CH:13][CH:12]=2)=[CH:6][CH:5]=1.CCN(C(C)C)C(C)C.[CH2:46]([O:48][C:49](=[O:53])[C:50](Cl)=[O:51])[CH3:47]>C(Cl)Cl>[O:51]=[C:50]([N:9]([CH2:8][C:7]1[CH:6]=[CH:5][C:4]([C:3]([F:2])([F:35])[F:36])=[CH:34][CH:33]=1)[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[O:21][N:20]=[C:19]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[N:18]=2)=[CH:15][CH:16]=1)[C:49]([O:48][CH2:46][CH3:47])=[O:53]

Participants

Conditions

Temperature: 0 °C

Procedure

To a cold (0° C.) solution of N-[4-(trifluoromethyl)benzyl]-N-[4-(3-undecyl-1,2,4-oxadiazol-5-yl)benzyl]amine hydrochloride (45 mg, 0.09 mmol) and DIEA (24 mg, 0.19 mmol) in anhydrous DCM (1 mL) was added dropwise the chloro-oxo-acetic acid ethyl ester (24 mg, 0.19 mmol). The reaction mixture was stirred at 0° C. for 3 h. Evaporation of the solvents under vacuum gave an orange oil. This crude product was purified by column chromatography over silica gel (AcOEt/c-Hex 1/9) to give the title compound as a colorless oil (38 mg, 75%). 1H NMR (CDCl3, 300 MHz) δ 8.10 (d, J=8.3 Hz, 1H), 8.02 (d, J=8.3 Hz, 1H), 7.56 (d, J=8.2 Hz, 1H), 7.53 (d, J=8.2 Hz, 1H), 7.39-7.21 (m, 4H), 4.50 (s, 2H), 4.37 (s, 2H), 4.29 (dq, J1=7.1 Hz, J2=2.3 Hz, 2H), 2.72 (t, J=7.4 Hz, 2H), 1.85-1.65 (m, 2H), 1.41-1.05 (m, 19H), 0.89 (t, J=7.0 Hz, 3H). HPLC (Condition A), Rt: 7.5 min (HPLC purity: 88.8%).

Workup

customEvaporation of the solvents under vacuum
customgave an orange oil
customThis crude product was purified by column chromatography over silica gel (AcOEt/c-Hex 1/9)

Sources & evidence

ORD record: ord-a13c610ad37742ab9e94f92bbf362c53
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592477B2

Reaction notes

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