Hydrochloric Acid → (R)-5-(allyloxyamino)-4-(2-amino-2-oxoethyl)-1,2,5,6-tetrahydropyridine-2-carboxamide

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Reaction Steps

To a solution of (2S)-tert-butyl 5-((allyloxy)amino)-4-(2-amino-2-oxoethyl)-2-carbamoyl-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 176, crude, 330 mg, 0.93 mmol) in DCM (5.0 mL) at 0° C. was added HCl (4.0M in dioxane, 0.233 mL, 0.93 mmol). The mixture was stirred from 0° C. to room temperature for 2 h. Then 0.233 mL more HCl was added to the mixture and stirred for 2 h. It was neutralized by K2CO3 and TEA, filtered and the solvent was removed under vacuum. The crude was subjected to silica column eluting with 0-50% MeOH/DCM to give the desired diastereomeric products as white solids. 100 mg, diastereomer 1. 32 mg, diastereomer 2. 56% yield.

Provenance & Evidence