Diisopropylcarbodiimide → HCID 86709971, compound

Participants

Reaction Steps

A mixture of 2-(3-hydroxy-5-((5-hydroxy-1,4,5,6-tetrahydropyrimidin-2-yl)amino)benzamido)acetic acid (Example B) (197.22 mg, 0.64 mmol), (S)-ethyl 3-amino-3-(3-bromo-5-(1-(difluoromethyl)cyclopropyl)phenyl)propanoate hydrochloride salt (from step 1 above) (253 mg, 0.635 mmol) and 1-hydroxybenzotriazole hydrate (19.44 mg, 0.127 mmol) was dissolved in a mixture of DMF/DCM (1:1) (8 mL) and stirred at room temperature under nitrogen atmosphere for 10 min to give a cream suspension. N,N′-diisopropylcarbodiimide (142 μL, 0.917 mmol) was added to the above suspension and the reaction mixture was stirred at room temperature overnight (16 h) under nitrogen atmosphere. The solvent was evaporated in vacuo to give a yellow gummy residue of the intermediate product. LC-MS analysis shows the desired product: (3S)-ethyl 3-(3-bromo-5-(1-(difluoromethyl)cyclopropyl)phenyl)-3-(2-(3-hydroxy-5-((5-hydroxy-1,4,5,6-tetrahydropyrimidin-2-yl)amino)benzamido)acetamido)propanoate's mass: m/z 652 (79BrM+H), m/z 654 (81BrM+H). The crude residue will be used as such for the saponification with lithium hydroxide monohydrate (Step 3).

Provenance & Evidence