Veratric Acid → HCID 66653252, compound

Participants

Reaction Steps

Stir a solution of 3,4-dimethoxybenzoic acid (2.318 g, 12.59 mmol) and CDI (2.063 g, 12.59 mmol) in DMF (75 mL) at room temperature for 1 h. To this add 3-((R)-1-amino-2-carboxy-ethyl)-benzoic acid N,N-dimethyl-formamide complex HCl salt (1.606 g, 5.04 mmol) followed by Et3N (2.47 mL, 17.63 mmol), and stir the solution at room temperature for 24 h. Remove the DMF in vacuo at 40° C. and dry the residue to a gum. Redissolve in EtOAc (200 mL). Wash with 0.5 M HCl (200 mL) then water (200 mL) and brine (100 mL). Extract the aqueous layers with more EtOAc (200 mL), and dry the organics (Na2SO4) then concentrate to a gummy residue. Purify this by silica gel chromatography eluting with 50% hexane/EtOAc to 100% EtOAc. Pool fractions containing desired product (Rf=0.10 100% EtOAc) and triturate the residue in EtOAc/hexane to afford 693 mg 3-[(R)-2-carboxy-1-(3,4-dimethoxy-benzoylamino)-ethyl]-benzoic acid as a solid.

Provenance & Evidence