Hydrochloric Acid → HCID 57062134, compound

Participants

Reaction Steps

A solution of crude lithium 4-((αR*)-α-((2R*,5S*)-2,5-dimethyl-1-piperazinyl)-3-tert-butyldimethylsiloxybenzyl)benzoate (11.5 g, from 23 mmol of Example 2 by the procedure of Example 6, Method B) in tetrahydrofuran was treated with 6M aqueous hydrochloric acid at room temperature for 18 hours. After dilution with water, the mixture was extracted with diethyl ether and the aqueous layer was adjusted to pH 8 with aqueous sodium hydroxide and extracted with dichloromethane. The aqueous layer was titrated to pH 6 with concentrated hydrochloric acid and the precipitated solid was collected by filtration, washed with water and dried under vacuum (60° C.) to give 2.65 g (30%) of (±)-4-((αR*)-α-((2R*,5S*)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-hydroxybenzyl)benzoic acid as an off-white powder. NMR (DMSO-d6) δ: 0.9 (d, J=6 Hz, 3H); 1.05 (d, J=6 Hz, 3H); 1.8 (dd, J1 =11 Hz, J2 =7 Hz, 1H); 2.1 (dd, J1 =11 Hz, J2 =7 Hz, 1H); 2.5 (m, 6H); 2.7 (d, J=11 Hz, 1H); 2.9 (dd, J1 =7 Hz, J2 =14 Hz); 3.1 (dd, J1 =14 Hz, J2 =5 Hz, 1H); 4.9-5.2 (m, 3H); 5.6-5.8 (m, 1H); 6.5 (dd, J1 =8 Hz, J2 =2 Hz, 1H); 6.8 (m, 2H); 7.1 (t, J=8 Hz, 1H); 7.3 (m, 1H); 7.4 (d, J=8 Hz, 2H); 7.9 (d, J=8 Hz, 2H). Calc. for C23H28N2O3 1.25 H2O: C, 68.55; H, 7.63; N, 6.95. Found: C, 68.61; H, 7.66; N, 7.02. Mass spectrum (Cl--CH4): m/z 381 (M+1, 44%), 153 (100%), 227 (17%).

Provenance & Evidence