Methyl chloroformate → HCID 59191808, compound

Participants

Reaction Steps

To 85G (1.25 g, 3.74 mmol) in pyridine (8.0 mL) at 0° C. was added methyl chloroformate (0.4 mL, 5.23 mmol). After 30 min, the reaction was quenched by MeOH (2.0 mL). Pyridine was removed under high vacuum. The crude was suspended in EtOAc and washed by 1.0 N HCl (2×20 mL), sat. NaHCO3 and brine. The organic layer was dried over Na2SO4. After evaporation of solvent, 85H (1.6 g, 95% yield) was obtained as a solid used for next step without purification. 1H NMR (400 MHz, DMSO-d6, 100° C.) δ ppm 0.52-0.64 (m, 2H) 0.94-1.05 (m, 2H) 1.17-1.28 (s, 9H) 1.54-1.63 (m, 1H) 1.77-1.86 (m, 2H) 2.18-2.29 (m, 2H) 3.46-3.57 (m, 2H) 3.62-3.68 (s, 3H) 5.05 (dd, J=7.70, 3.85 Hz, 1H) 7.23 (s, 1H) 7.32-7.40 (m, 1H) 7.40-7.47 (m, 1H) 9.26 (s, 1H), LC-MS 293 (M-Boc).

Provenance & Evidence