Guide of Tert-butyl 4,4,4-Trifluoro-3-(Trifluoromethyl)But-2-Enoate

Tert-butyl 4,4,4-trifluoro-3-(trifluoromethyl)but-2-enoate is mainly used for the synthesis of uracil and its derivatives, sulfonamides herbicide.
Imformation of Tert-butyl 4,4,4-trifluoro-3-(trifluoromethyl)but-2-enoate :
Molecular Formula:C9H10F6O2

Molecular Weight: 264.16 g/mol

Addition of various amines to the 3,3-bis(trifluoromethyl)acrylamides 10a and 10b gave the tripeptides 11a–11f, mostly as mixtures of epimers (Scheme 3). The crystalline tripeptide 11f₂ was found to be the N-terminal (2-hydroxyethoxy)-substituted (R,S,S)-ester HOCH₂CH₂O-D-Val(F₆)-MeLeu-Ala-O^tBu by X-ray crystallography. The C-terminal-protected tripeptide 11f₂ was condensed with the N-terminus octapeptide 2b to the depsipeptide 12a which was thermally rearranged to the undecapeptide 13a (Scheme 4). The condensation of the epimeric tripeptide 11f₁ with the octapeptide 2b gave the undecapeptide 13b directly. The undecapeptides 13a and 13b were fully deprotected and cyclized to the [5-[4,4,4,4′,4′,4′-hexafluoro-N-(2-hydroxyethoxy)-D-valine]]- and [5-[4,4,4,4′,4′,4′-hexafluoro-N-(2-hydroxyethoxy)-L-valine]]cyclosporins 14a and 14b, respectively (Scheme 5). Rate differences observed for the thermal rearrangements of 12a to 13a and of 12b to 13b are discussed.

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