Ammonia → tert-Butyl [(3S,5S,6S,8S)-8-[(3-amino-2,2-dimethyl-3-oxopropyl)carbamoyl]-6-hydroxy-3-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-2,9-dimethyldecan-5-yl]carbamate

Participants

Reaction Conditions

Reaction Steps

A solution of 0.037 g of amide 12 is dissolved in 1 mL of tetrahydrofurane and cooled to −78° C. Liquid ammonia is added followed by 0.0042 g of lithium metal. The deep blue solution is stirred for 2 hours at −78° C., and then 0.35 g of ethanol is added and the mixture is stirred for 30 minutes at −78° C. Ammonium chloride (0.15 g) is added and the mixture is warmed to room temperature. The organic phase is partitioned between water and ethyl acetate. The organic phase is separated and the solvent removed in vacuum. The residue is stirred with heptane and filtered. Removal of the heptane produces 13 identical with an authentic sample. M++H=652

Provenance & Evidence