Ethylenediamine → HCID 44224224, compound

Participants

Reaction Steps

tert-Butyl (8R)-8-(3,5-difluorophenyl)-8-methyl-10-oxo-9-[(2E)-3-(2′-oxo-1′-{[2-(trimethylsilyl)ethoxy]methyl}-1,1′,2′,3-tetrahydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-5-yl)prop-2-en-1-yl]-6,9-diazaspiro[4.5]decane-6-carboxylate from Step A above (0.2276 g, 0.290 mmol) was dissolved in DCM (5 mL). To this solution was added 1 mL of TFA. The reaction was stirred for 24 hours, then concentrated in vacuo. The residue was dissolved in MeOH (5 mL) and to this solution was added 1N NaOH (2.90 ml, 2.90 mmol), and ethylenediamine (0.078 ml, 1.160 mmol). The reaction was stirred for ½ hour at RT, then concentrated in vacuo. The residue was partitioned between ethyl acetate and water. The layers were separated, then the aqueous layer was washed 3×20 mL with ethyl acetate. The combined organic layers were washed with brine. Dried over Magnesium sulfate, filtered and concentrated in vacuo to yield the title compound. Diastereomer separation was accomplished using a Chiralcel OJ column, eluting with CO2:MeOH—70:30. Two peaks were isolated. Peak 1 MS: m/z=555 (M+1) HRMS: m/z=555.2569 (M+1); calculated m/z=555.2566 (M+1) for C33H32F2N4O2, and Peak 2 MS: m/z=555 (M+1)HRMS: m/z=555.2569 (M+1); calculated m/z=555.2566 (M+1) for C33H33F2N4O2.

Provenance & Evidence