303049-60-7

Basic information

• Product Name: N^α-2,2,2-trifluoroethylphenylalanine tert-butyl ester
• CAS NO: 303049-60-7
• Molecular Weight: 303.325
• Mol File: 303049-60-7.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: N^α-2,2,2-trifluoroethylphenylalanine tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N^α-2,2,2-trifluoroethylphenylalanine tert-butyl ester(303049-60-7)
• EPA Substance Registry System: N^α-2,2,2-trifluoroethylphenylalanine tert-butyl ester(303049-60-7)

Safety Data

• Hazardous Substances Data: 303049-60-7(Hazardous Substances Data)

Upstream product

• 15100-75-1 L-phenylalanine tert-butyl ester hydrochloride 
• 307501-98-0 (1,1,1-trifluoroethyl) phenyl iodonium (N,N'-bis-trifluoromethylsulfonyl) imide 
• 16874-17-2 L-phenylalanine tert-butyl ester 

Relevant articles and documents

A discovery tool at work: The unexpected properties of a two-carbon residue

We report the very easy preparation of novel peptides 6a-n as represented by CF3CH2(L)Phe(L)IleOtBu (6a), a prospective antitumor compound. Peptides such as 6a are directly obtained via standard chemistry from a novel class of amino acids, Nα-trifluoroethyl amino acids 4. In fact, unexpectedly, the Nα-1,1,1-trifluoroethyl substitution completely deactivates the α-nitrogen. That is, compounds 4 behave exactly like Nα-protected amino acids, and take part in standard peptide synthesis accordingly. Representative compounds 4a-c are prepared by reaction of commercial amino acid t-butyl esters 2a-c with 1 eq iodonium salt 1 in dichloromethane/water at 22°C in 1 h or less. The reaction is promoted by NaHCO3 (1.5 eq). The intermediate Nα-1,1,1-trifluoroethyl t-butyl esters 3a-c are hydrolyzed and separated from coproducts at the same time by treatment with aqueous HCl at 22°C. Evaporation of the acid extracts provides analytically pure 4a-c in 78-98% yields.