1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59437171, compound

Participants

Reaction Steps

To a solution of (1-adamantyl)methylamine (100 mg, 0.61 mmol), (S)-2-hydroxy-2-phenylacetic acid (92 mg, 0.61 mmol), EDCI (239 mg, 1.22 mmol) and HOBt (164 mg, 1.22 mmol) in CH2Cl2 (15 mL) was added DIEA (391 mg, 3.03 mmol) and the resulting mixture was stirred overnight. The solution was concentrated under vacuum to give the crude product, which was purified by preparative TLC to afford (S)—N-((1-adamantyl)methyl)-2-hydroxy-2-phenylacetamide (85 mg, 47%). 1H NMR (CDCl3, 400 MHz): δ=1.34-1.91 (m, 15H), 2.86 (q, 1H), 3.02 (q, 1H), 5.04 (s, 1H), 5.93 (s, 1H), 7.25-7.43 (m, 5H).

Provenance & Evidence