Dichloromethane → HCID 72950867, compound

Participants

Reaction Steps

To a suspension of (3S)-ethyl 3-(2-(3-hydroxy-5-((5-hydroxy-1,4,5,6-tetrahydropyrimidin-2-yl)amino)benzamido) acetamido)-3-(3-(1,1,1-trifluoro-2-hydroxypropan-2-yl)-5-(trifluoromethyl)phenyl)propanoate (from step 2 above) (˜708 mmol, crude residue) in a mixture of acetonitrile/water (1:1) (6 mL) was added lithium hydroxide mono hydrate (150 mg, 3.575 mmol) and the reaction mixture was stirred at room temperature overnight. The solvent was evaporated in vacuo to afford a yellow-orange viscous residue. The residue was dissolved in water (25 mL) and stirred with dichloromethane (50 mL) to remove the urea. The aqueous layer was neutralized with TFA (1 mL in 3 mL ACN) and evaporated in vacuo to afford a pale viscous residue. The crude residue was purified by reverse-phase preparative HPLC on a Biotage 40+M (100 g) C18HS column and a gradient 10-60% acetonitrile in water containing 0.05% TFA to give the desired product, after lyophilzation, as a colorless lyophilized powder (287.8 mg). LC-MS analysis of the solid shows the desired product's mass: m/z 636 (M+H); Calcd for C26H27F6N5O7: 635.51

Provenance & Evidence