Hydrochloric Acid → HCID 67071618, compound

Participants

Reaction Steps

(±)-(E)-3-[1′-(2-Phenyl-ethyl)-4-oxo-spiro[chromane-2,4′-pyrrolidine]-6-yl]-acrylic acid methyl ester (280 mg, 0.71 mmol) was hydrolyzed with HCl and AcOH following the procedure described in Example 1, Step A, giving (±)-(E)-3-[1′-(2-phenyl-ethyl)-4-oxo-spiro[chromane-2,4′-pyrrolidine]-6-yl]-acrylic acid as a white solid (288 mg, 98%). The acid was treated with NH2OTHP according to the procedure described in Example 1, Step C, giving (E)-3-[1′-(2-phenyl-ethyl)-4-oxo-spiro[chromane-2,4′-pyrrolidine]-6-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide as a yellow solid (103 mg, 0.22 mmol, 31%). Finally, removal of THP protecting group following the procedure described in Example 1, Step D gave (±)-(E)-3-[1′-(2-phenyl-ethyl)-4-oxo-spiro[chromane-2,4′-pyrrolidine]-6-yl]-N-hydroxy-acrylamide hydrochloride (33.7 mg, 36%) as a white solid.

Provenance & Evidence