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tert-Butyloxycarbonyl protecting group. The tert-butyloxycarbonyl protecting group or tert-butoxycarbonyl protecting group [1] (BOC group) is an acid-labile protecting group used in organic synthesis. The BOC group can be added to amines under aqueous conditions using di-tert-butyl dicarbonate in the presence of a base such as sodium hydroxide:
The Boc group can later be removed from the amine using moderately strong acids (e.g., trifluoroacetic acid). Thus, Boc serves as a protective group, for instance in solid phase peptide synthesis. Boc-protected amines are unreactive to most bases and nucleophiles, allowing for the use of the fluorenylmethyloxycarbonyl group (Fmoc) as an ...
Fmoc/tBu SPPS is less atom-economical, as the fluorenyl group is much larger than the Boc group. Accordingly, prices for Fmoc amino acids were high until the large-scale piloting of one of the first synthesized peptide drugs, enfuvirtide, began in the 1990s, when market demand adjusted the relative prices of Fmoc- vs Boc- amino acids.
Orthogonal protection is a strategy allowing the specific deprotection of one protective group in a multiply-protected structure. For example, the amino acid tyrosine could be protected as a benzyl ester on the carboxyl group, a fluorenylmethylenoxy carbamate on the amine group, and a tert-butyl ether on the phenol
Di-tert-butyl-iminodicarboxylate is an organic compound that can be described with the formula [(CH 3) 3 COC(O)] 2 NH.It is a white solid that is soluble in organic solvents. The compound is used as a reagent for the preparation of primary amines from alkyl halides
The fluorenylmethoxycarbonyl protecting group (Fmoc) is a base-labile amine protecting group used in organic synthesis, particularly in peptide synthesis. [1] It is popular for its stability toward acids and hydrolysis and its selective removal by weak bases, such as piperidine , without affecting most other protecting groups or sensitive ...
This heterocyclic amine consists of a six-membered ring containing five methylene bridges (–CH 2 –) and one amine bridge (–NH–). It is a colorless liquid with an odor described as objectionable, typical of amines. [6] The name comes from the genus name Piper, which is the Latin word for pepper. [7]
The symmetrical structure [clarification needed] of α-phenyl propanamide does not change after Hofmann reaction. In the synthesis of gabapentin , beginning with the mono-amidation of 1,1-cyclohexane diacetic acid anhydride with ammonia to 1,1-cyclohexane diacetic acid mono-amide, followed by a Hofmann rearrangement [ 12 ]