Trimethylsilyl triflate → L-Tyrosine

HRID 1709616Notes

Reaction equation

[NH2:1][C@H:2]([C:18]([OH:20])=[O:19])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10]CC2C=CC=CC=2)=[CH:6][CH:5]=1.C[Si](OS(C(F)(F)F)(=O)=O)(C)C>>[NH2:1][C@H:2]([C:18]([OH:20])=[O:19])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1

Participants

Reactant 2

HCID 65367Trimethylsilyl triflate

HCID 725701O-benzyl-L-tyrosine

Product 1

HCID 6057L-TyrosineYield 100%

Procedure

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.

Workup

customthioanisle/trifluoroacetic acid from which anisole is removed

Sources & evidence

ORD record: ord-9dfd3b8256cd447fba86125226257190
Source dataset: uspto-grants-1990_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04950418

Reaction notes

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