Lithium Hydroxide → HCID 118380493, compound

Participants

Reaction Steps

In a 100 mL round-bottomed flask, (S)-ethyl 1-((S)-2-((S)-2-(tert-butoxycarbonyl(methyl)amino)propanamido)-2-(tetrahydro-2H-pyran-4-yl)acetyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate (188 mg, 363 μmol, Eq: 1.00) was combined with THF (3 mL) and ethanol (1 mL) to give a colorless solution. Aqueous 1 M LiOH (1.1 mL, 1.1 mmol, Eq: 3) was added and the reaction was stirred at rt for 1 h. Aqueous 0.1 M KHSO4 (10 mL) was added and the resulting mixture was extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated in vacuo to give (S)-1-((S)-2-((S)-2-(tert-butoxycarbonyl(methyl)amino)propanamido)-2-(tetrahydro-2H-pyran-4-yl)acetyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid (135 mg), m/z=491 (M+H).

Provenance & Evidence