Water → 3-(4-Ethoxy-2-oxocyclohex-3-enyl)propyl 2-(methylamino)benzoate

HRID 77270

Reaction equation

[CH2:1]([O:3][C:4]1[CH2:9][CH2:8][CH:7]([CH2:10][CH2:11][CH2:12][OH:13])[C:6](=[O:14])[CH:5]=1)[CH3:2].CCN(CC)CC.[CH3:22][N:23]1C(=O)O[C:26](=[O:27])[C:25]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:24]12.O>CN(C1C=CN=CC=1)C.CN(C=O)C>[CH3:22][NH:23][C:24]1[CH:34]=[CH:33][CH:32]=[CH:31][C:25]=1[C:26]([O:13][CH2:12][CH2:11][CH2:10][CH:7]1[CH2:8][CH2:9][C:4]([O:3][CH2:1][CH3:2])=[CH:5][C:6]1=[O:14])=[O:27]

Participants

Conditions

Temperature: 65 °C

Procedure

Alcohol 3 (180 mg, 0.89 mmol), NEt3 (0.56 mL) and catalytic DMAP were added to a solution of N-methylisatoic anhydride (220 mg, 0.89 mmol) in dry DMF (2.0 mL) at rt. After stirring overnight, the solution was warmed to 65° C. for 3 h. After cooling to rt, water was added and this mixture was extracted with ethyl acetate (5×50 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and evaporated to give the crude product, which was purified by flash column chromatography to afford 87.0 mg (45% yield) of 4 as a white solid: 1H NMR (300 MHz, CDCl3) δ 7.85 (1H, m), 7.33 (1H, m), 6.56 (2H, m), 5.27 (1H, s), 4.22 (2H, t, J=5.2 Hz), 3.85 (2H, q, J=7.0 Hz), 2.86 (3H, s), 2.39 (2H, t, J=5.3 Hz), 2.04-1.41 (7H, m), 1.31 (3H, t, J=7.0 Hz); 13C NMR (75 MHz, CDCl3) δ 201.1, 176.8, 168.7, 151.7, 134.7, 131.7, 115.0, 111.3, 110.6, 102.5, 101.9, 64.7, 64.5, 64.3, 44.9, 30.0, 28.2, 26.6, 26.5, 26.4, 14.3; ESI MS m/z 354 (M++Na+).

Workup

temperatureAfter cooling to rt
extractionthis mixture was extracted with ethyl acetate (5×50 mL)
washThe combined organic layers were washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
customevaporated
customto give the crude product, which
customwas purified by flash column chromatography

Sources & evidence

ORD record: ord-958ff28899cb4cf1895dc65cd340913b
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841132B2

Linked notes

Loading…