1-Piperazinecarboxylic acid, ethyl ester → Ethyl 4-[(5,6-dioxo-2,3,5,6-tetrahydronaphtho[1,2-b][1,4]oxathiin-2-yl)methyl]piperazine-1-carboxylate

HRID 563117Notes

Reaction equation

CS(O[CH2:6][CH:7]1[O:12][C:11]2[C:13]3[C:18]([C:19](=[O:22])[C:20](=[O:21])[C:10]=2[S:9][CH2:8]1)=[CH:17][CH:16]=[CH:15][CH:14]=3)(=O)=O.[N:23]1([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.C(N(CC)CC)C>CS(C)=O>[O:21]=[C:20]1[C:10]2[S:9][CH2:8][CH:7]([CH2:6][N:26]3[CH2:25][CH2:24][N:23]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:28][CH2:27]3)[O:12][C:11]=2[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:19]1=[O:22]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of (5,6-dioxo-2,3,5,6-tetrahydronaphtho[1,2-b][1,4]oxathiin-2-yl)methyl methanesulfonate (0.15 g, 0.44 mmol) in DMSO (1.5 mL) was added ethyl piperazine-1-carboxylate (0.065 mL, 0.88 mmol) and triethylamine (0.12 mL, 0.88 mmol). The reaction mixture was shaken at 50° C. for 2 hours. The crude product was purified by reverse phase HPLC to give the desired product as a purple solid (0.015 g, 5%). M.p.=185-187° C.; 300 MHz 1H NMR (CDCl3) δ: 8.04 (d, J=7.2 Hz, 1H), 7.66 (m, 2H), 7.48 (t, J=7.2 Hz, 1H), 4.66 (m, 1H), 4.15 (m, 2H), 3.51 (m, 4H), 3.23 (m, 1H), 3.03 (m, 1H), 2.83 (m, 2H), 2.54 (m, 4H), 1.27 (m, 3H); LCMS: 403 [M+H].

Workup

customThe crude product was purified by reverse phase HPLC

Sources & evidence

ORD record: ord-28641aa988ad4c4f838635002eba10e5
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067459B2

Reaction notes

Loading…