Acetic Acid → HCID 86660245, compound

Participants

Reaction Steps

To a stirred solution of ethyl (5S)-5-amino-5-(3,5-difluorophenyl)-2,2-dimethylpentanoate from Step A (˜82.0 mg, 0.289 mmol) and (7S)-2′-oxo-1′, 2′,6,8-tetrahydrospiro[cyclopenta[g]quinoline-7,3′-pyrrolo[2,3-b]pyridine]-3-carbaldehyde (91.0 mg, Intermediate 1) in dry chloroform (3 mL) was added HOAc (35 μL, 0.606 mmol). After 10 minutes, sodium triacetoxyborohydride (129 mg, 0.606 mmol) was added. After 80 minutes of stifling, the reaction mixture was diluted with DCM (30 mL) and saturated sodium bicarbonate (20 mL). The layers were separated and the aqueous layer was extracted once with DCM (20 mL). The combined organics were dried over sodium sulfate, filtered and concentrated in vacuo to provide a residue. This residue was applied to a silica gel column for purification, eluting with a gradient of CH2Cl2:MeOH—99:1 to 93:7. Clean product-containing fractions were pooled and concentrated in vacuo to give the title compound, which still contained about 30% of the methyl ester. MS: m/z=585 (M+1).

Provenance & Evidence