Sodium Hydroxide → HCID 66932583, compound

Participants

Reaction Steps

(E)-3-{1′-[2-(1H-indol-3-yl)ethyl]-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid methyl ester (129 mg, 0.29 mmol) was hydrolyzed with 4 M NaOH following the procedure described in Example 40, Step B, giving (E)-3-{1′-[2-(1H-indol-3-yl)ethyl]-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid (109 mg, 87%). The product was treated with NH2OTHP according to the procedure described in Example 40, Step C, giving (E)-3-{1′-[2-(1H-indol-3-yl)ethyl]-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-N-(tetrahydro-pyran-2-yloxy)-acrylamide. Removal of the THP protecting group following the procedure described in Example 40, Step C gave (E)-3-{1′-[2-(1H-indol-3-yl)ethyl]-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-N-hydroxy-acrylamide, which was purified by preparative LC-MS and obtained as its trifluoroacetate salt (37 mg, white solid).

Provenance & Evidence