Hydrochloric Acid → HCID 67071578, compound

Participants

Reaction Steps

(±)-(E)-3-[1′-Acetyl-4-oxo-spiro(chromane-2,3′-pyrrolidine)-6-yl]-acrylic acid methyl ester (240 mg, 0.73 mmol) was hydrolyzed with HCl and AcOH following the procedure described in Example 1, Step A, giving (±)-(E)-3-[1′acetyl-4-oxo-spiro(chromane-2,3′-pyrrolidine)-6-yl]-acrylic acid as a white solid (135.5 mg, 0.43 mmol, 59%). The acid was treated with NH2OTHP according to the procedure described in Example 1, Step C, giving (E)-3-[1′-acetyl-4-oxo-spiro(chromane-2,3′-pyrrolidine)-6-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide as a light yellow solid (82 mg, 0.20 mmol, 46%). Finally, removal of THP protecting group following the procedure described in Example 2, Step D gave (±)-(E)-3-[1′-acetyl-4-oxo-spiro(chromane-2,3′-pyrrolidine)-6-yl]-N-hydroxy-acrylamide (64.2 mg, 97%) as a red solid.

Provenance & Evidence