L-Tartaric acid → HCID 86649829, compound

Participants

Reaction Conditions

Reaction Steps

A solution containing 3.9 g (26 mmol) of L-tartaric acid and 36 mL of methanol was added to a solution of 9 g (26 mmol) of arformoterol base and 144 mL methanol at 23° C. Afterwards, the resulting mixture was seeded with form D and stirred at 23° C. for 1 hour. It was then further cooled to 0-5° C. for 1 hour and the product collected by filtration and dried under inlet air (atmospheric pressure) for 16 hours to provide 11.1 g (86% yield) (99.7% chemical purity, containing 0.14% of the degradation impurity (R)-1-(3-amino-4-hydroxyphenyl)-2-[[(1R)-2-(4-methoxyphenyl)-1-methylethyl]amino]ethanol) of (R,R)-formoterol L-tartrate form D, as an off white powder. 1H-NMR (200 MHz, d6-DMSO) δ: 1.03 (d, 3H); 2.50-2.67 (m, 5H); 3.72 (s, 3H); 3.99 (s, 2H); 4.65-4.85 (m, 1H); 6.82-7.15 (m, 5H); 8.02 (s, 1H); 8.28 (s, 1H); 9.60 (s, NH). No residual solvent was detected (1H-NMR).

Provenance & Evidence