Methyl 1-([(3S)-3-[(2-oxo-2-{[(2R)-2'-oxo-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-yl]amino]ethyl)amino]-3-phenylpropyl}amino)cyclo-pentanecarboxylate → Potassium 1-({(3S)-3-[(2-oxo-2-{[(2R)-2'-oxo-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-yl]amino}ethyl)amino]-3-phenylpropyl}amino)cyclo-pentanecarboxylate

Participants

Reaction Steps

To a stirred solution of methyl 1-({(3S)-3-[(2-oxo-2-{[(2R)-2′-oxo-1,1′,2′,3-tetrahydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-5-yl]amino}ethyl)amino]-3-phenylpropyl}amino)cyclopentanecarboxylate from Step A (0.141 g, 0.249 mmol) in dry THF (5 mL) was added KOTMS (64.0 mg, 0.498 mmol) and the reaction mixture was heated to 40° C., at which point the desired product began to precipitate. Two additional quantities of KOTMS (˜60 mg×2) were added over the next 2 h resulting in a complete consumption of starting material. The mixture was then allowed to cool to ambient temperature. The THF, which contained only traces of product, was then decanted away from the precipitated product. This solid was then washed with two additional quantities of anhydrous THF (5 mL×2), to provide the title compound. MS: m/z=554 (M+1).

Provenance & Evidence