Hydrochloric Acid → HCID 71547277, compound

Participants

Reaction Conditions

Reaction Steps

(R)-Methyl 2-acetamido-3-(2-(3,3-dinitroazetidin-1-yl)-2-oxoethylthio)propanoate (1.02 g, 2.80 mmol) was dissolved in methanol (50 mL) with stirring and the mixture cooled to 0° C. Then, LiOH (0.5 M, 8.40 mL) was added dropwise to the reaction mixture via a syringe and the resulting yellow mixture stirred until TLC showed complete conversion (2.5 hours). Next, the reaction mixture was diluted with water, cooled to 0° C. and acidified to pH=2 with a 50% HCl solution. Then, the reaction mixture was extracted with ethyl acetate (×2) and the extracts were dried over Na2SO4, filtered and concentrated under reduced pressure to provide a residue that was purified by column chromatography using silica gel and 30% MeOH in EtOAc as eluent to provide the title compound 625 mg (64%) as a white solid. 1H NMR (200 MHz, DMSO-d6) δ 1.85 (s, 3H), 2.81 (dd, 1H, J=8.4, 13.6 Hz), 3.04 (dd, 1H, J=4.8, 13.6 Hz), 3.33 (s, 2H), 4.41-4.35 (m, 1H), 4.80 (s, 2H), 5.13 (s, 2H), 8.20 (d, 1H, J=8.0 Hz). LC/MS (M+H=351). The purity was checked using LC/MS using Phenomenex Luna 3μ C8 (2) 100 A column using water with 0.1% TFA and acetonitrile with 0.1% as mobile phase (30-90% acetonitrile @ 1.0 mL/min). Retention time=0.60 mins; Area %=97.6%.

Provenance & Evidence