Trimethylsilyldiazomethane → HCID 86710402, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-2-((tert-butoxycarbonyl)amino)-4-methylpent-4-enoic acid (550 mg, 2.399 mmol) in tetrahydrofuran (11 mL) at 0° C., was added TMS-diazomethane (4.80 mL, 4.80 mmol) dropwise over 5 min. The reaction mixture was then stirred at 0° C. for 15 min. After gradually warmed to room temperature, the mixture was stirred for 16 h. The reaction mixture was evaporated to dryness to afford (S)-methyl 2-((tert-butoxycarbonyl)amino)-4-methylpent-4-enoate (580 mg, 2.386 mmol, 99% crude yield) as a dark yellow oil which was taken to the next step without purification. 1H NMR (400 MHz, CDCl3): δ ppm 4.91 (s, 1H), 4.85 (s, 1H), 4.75 (s, 1H), 4.38 (q, J=16.00 Hz, 1H), 3.73 (s, 3H), 2.33-2.53 (m, 2H), 1.71 (s, 3H), 1.43 (s, 9H).

Provenance & Evidence