Trimethylsilyl triflate → L-Tyrosine

Participants

Reaction Steps

As a comparative example, Tyr(Bzl) was treated with a deprotecting reagent of 1M trimethylsilyltrifluoromethanesulfonate and thioanisle/trifluoroacetic acid from which anisole is removed to get Tyr. The yield of Tyr after 10 minutes was 64% and the formation of 3-Bzl-Tyr due to rearrangement was observed. The same reaction was repeated except that hydrogen fluoride was used in place of trimethylsilyltrifluoromethanesulfonate, then Tyr was recovered in an yield of approximately 100% within 10 minutes. However, the product contained 35% of 3-Bzl-Tyr as a by-product.

Provenance & Evidence