Hydrochloric Acid → HCID 56602332, compound

Participants

Reaction Steps

A solution of 287 mg (0.67 mmol) of ethyl 3-{4-[2-(2-isopropyl-5-methylphenoxy)-propionylamino]phenyl}-3-methoxypropionate in 10 ml of 2N NaOH/THF/NaOH in a ratio of 1:1:1 was left to stand at RT for 30 minutes. The reaction mixture was admixed with water and adjusted to pH=6-7 with 1 N HCl (aq) and then extracted with ethyl acetate. The organic phase was dried over MgSO4, filtered and concentrated under high vacuum. The crude mixture was purified by means of preparative HPLC (Merck Hibar Purospher Star RP-18e 10 μm 25×250 mm; A: H2O+0.05% TFA; B: ACN+0.05% TFA; flow rate: 50 ml/min; in 10 minutes 10% B→80% B; in 10 minutes 80% B→90% B). This gave 138 mg of 3-{4-[2-(2-isopropyl-5-methylphenoxy)propionylamino]phenyl}-3-methoxypropionic acid in 51% yield over the two stages.

Provenance & Evidence