Hydrochloric Acid → HCID 10977104, compound

Participants

Reaction Conditions

Reaction Steps

A solution of the ester 7-6 (14.1 g, 26 mmol) in EtOAc (350 mL) cooled to -20° C. was treated with HCl (gas) for 10 minutes then stoppered and stirred at 0° C. for 1.5 hr. The volatiles were removed in vacuo, the residue taken up in 150 mL of water and treated with solid K2CO3 to pH~10. This solution was extracted with EtOAc (3×150 mL), washed with brine, dried (Na2SO4) and concentrated to give an oil. Column chromatography (silica gel; 5% MeOH in CHCl3) gave the β-alanine 7-5; further elution with 5% MeOH in CHCl3 saturated with NH3 gave 7-7 as a viscous oil. 1H NMR (300 MHz, CDCl3) δ 1.20 (3H, t), 1.8-1.95 (4H, m), 2.5-2.8 (12H, m), 3.39 (2H, m), 3.92 (3H, s), 4.09 (2H, q), 5.01 (1H, bs), 6.34 (1H, d), 6.72 (1H, d), 7.06 (1H, d), 7.59 (1H, dd), 8.07 (1H, d).

Provenance & Evidence