Hydrochloric Acid → HCID 69545714, compound

Reaction equation

[Mg].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][C:10]=2[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:5][CH:4]=1.Cl>CO>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[CH2:11][CH:10]2[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:7][CH:8]=1

Participants

Procedure

Magnesium metal (1.23 g, 51.0 mmol) was added in three portions over approximately 0.3 h to a stirred solution of the product of step D (1.85 g, 5.1 mmol) in methanol (40 mL) at ambient temperature. After stirring overnight, the reaction mixture was poured into 1 N hydrochloric acid (100 mL) and extracted three times with ethyl acetate. The combined organic extracts were washed with saturated sodium bicarbonate, brine, dried (MgSO4) and concentrated in vacuo. Purification of the residue by medium pressure liquid chromatography on silica gel (gradient elution; 0–25% ethyl acetate/hexanes as eluent) provided the title compound (mixture of cis/trans diastereoisomers) as a colorless oil (1.5 g).