Pentafluorosulfanyl containing amino acids
AssigneeThe Research Foundation of State University of New York
InventorJohn T. WELCH
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Abstract
There are provided SF5-containing amino acids of the general formulas and processes for preparing same. Other embodiments are also disclosed.
Claims32
A compound selected from the group consisting of formulae I-I, II-II, and III-III:
- or a salt thereof,
- wherein
- W is selected from
- W′ is selected from
- denotes a moiety selected from
- R1 is chosen from H and an amino protecting group;
- R2 is chosen from H and C1-C6 alkyl;
- R3 is independently at each occurrence chosen from C1-C6 alkylene and a direct bond;
- A is independently at each occurrence chosen from C1-C5 hydrocarbon and a direct bond;
- R4 is chosen from H, an amino protecting group, an amino acid, a peptide, and a protein;
- R5 is chosen from H, C1-C6 alkyl, an amino acid, a peptide, and a protein;
- R6 is independently at each occurrence chosen from H and C1-C2 alkyl and
- R7 is independently at each occurrence chosen from H and C1-C3 alkyl, and
- n is an integer of 1 or more.
A process for SF5X addition, wherein X is Br or Cl, comprising reacting a compound having an alkene functional group —CH═CH— with a solution of SF5X in (a) one more or C1-C3 chlorofluorocarbons, (b) one or more C5-C6 alkyls, or (c) a mixture of at least one C1-C3 chlorofluorcarbon and at least one C5-C6 alkyl, where said reacting yields an SF5X addition product
A compound of formula VIa, VIb, VIc or Vid:
- wherein
- R1 is chosen from H and an amino protecting group;
- R2 is chosen from H and C1-C6 alkyl;
- R8 is independently at each occurrence chosen from H and C1-C3 alkyl;
- R9 is independently at each occurrence chosen from —CH═CH2 and —CH2CH3;
- and
- R10 is chosen from H and an alcohol protecting group. In some embodiments, in the compound of formula VI, Y is NHBoc and Prot is trialkyl silyl.
A solution of SF5X in a solvent selected from (a) one or more C1-C3 chlorofluorocarbons, (b) one or more C5-C6 alkyls, and (c) a mixture of at least one C1-C3 chlorofluorocarbons and at least one C5-C6 alkyls, wherein X is selected from Br and Cl.
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A process for preparation of a compound of formula VI
- wherein R8 is H or alkyl, Prot is an enol protecting group, and Y is a protected amine, comprising reacting a compound of formula VII
- with a compound of formula VIII
- to obtain a compound of formula IX
- then reacting the compound formula IX with a strong, non-nucleophilic base, followed by reacting the resulting mixture with an enolate-reactive reagent for protecting an enol to obtain a compound of formula X
- and exposing the compound of formula X to conditions in which the compound of formula X rearranges to form a compound of formula VI.
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A compound of formula VI
- wherein R8 is H or alkyl, Prot is an enol protecting group, and Y is a protected amine.
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Dependencies are inferred from the claim text.