Diisopropylethylamine → Methyl 3-[(4-{[3-methyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}phenyl)amino]-3-oxopropanoate

HRID 1992841Notes

Reaction equation

C(N(C(C)C)C(C)C)C.[CH3:10][C:11]1[C:12]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[C:13]([O:23][C:24]2[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=2)[C:14]2[C:19]([CH:20]=1)=[CH:18][C:17]([O:21][CH3:22])=[CH:16][CH:15]=2.Cl[C:38](=[O:44])[CH2:39][C:40]([O:42][CH3:43])=[O:41]>C(Cl)Cl>[CH3:10][C:11]1[C:12]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[C:13]([O:23][C:24]2[CH:30]=[CH:29][C:27]([NH:28][C:38](=[O:44])[CH2:39][C:40]([O:42][CH3:43])=[O:41])=[CH:26][CH:25]=2)[C:14]2[C:19]([CH:20]=1)=[CH:18][C:17]([O:21][CH3:22])=[CH:16][CH:15]=2

Participants

Conditions

Temperature: 0 °C

Procedure

N-ethyldiisopropylamine (147 μL, 0.84 mmol, 3 equiv) was added to a solution of 38 (100 mg, 0.28 mmol, 1 equiv) in CH2Cl2 (5 mL) at 0° C. After 10 min, methyl 3-chloro-3-oxopropionate (60 μL, 0.56 mmol, 2 equiv) was added and the reaction was stirred at 0° C. for 3 h. The reaction mixture was diluted with CH2Cl2 (50 mL) and washed with saturated aqueous NaHCO3 (100 mL). The organic layer was dried over MgSO4, filtered, concentrated and the residue purified by silica gel flash column chromatography (30% EtOAc:hexanes) to provide 41 (87 mg, 68%) as a yellow oil. 1HNMR (400 MHz, DMSO-d6): δ 10.00 (s, 1H), 7.68 (s, 1H), 7.56 (m, 1H), 7.33-7.17 (m, 8H), 7.06-7.03 (m, 1H), 6.53 (m, 2H), 3.86 (s, 3H), 3.61 (s, 3H), 3.37 (s, 2H), 2.17 (s, 3H). MS m/z 455.87 (M+H)+.

Workup

washwashed with saturated aqueous NaHCO3 (100 mL)
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
concentrationconcentrated
customthe residue purified by silica gel flash column chromatography (30% EtOAc:hexanes)

Sources & evidence

ORD record: ord-acb8375f55a94ac2bb74e21e9a4f153f
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07649093B2

Reaction notes

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