Fluorenylmethyloxycarbonyl chloride

Precolumn derivatization methods include 1,2-diphenylethylenediamine treatment, dansylation of E, NE and DA, derivatization of NE and DA by o-phthalaldehyde and mercaptoethanol and derivatization of catecholamines with 9-fluorenylmethyloxycarbonyl chloride (FMOC-Cl). Derivatization with o-phthalaldehyde increases the sensitivity of NE and DA, but E is not measured because only primary amines are derivatized. Co-analysis of catecholamines, metanephrines and other related compounds by combined electrochemical oxidation and fluorescence derivatization had also been reported. ° This approach involves sequential chromatographic separation, coulometric oxidation and final chemical derivatization with 1,2-diphenylethylenediamine to fluorescent products. 

Molnar-Perl I. Advancement in the derivatization of the amino groups with o-phtha-laldehyde-thiol and with 9-fluorenylmethyloxycarbonyl chloride reagent. J Chromatogr B 2011 87 1241-69. 

LC-MS NH4OH, pH 10 and reversed phase SPE (water) Online derivatization using fluorenylmethyloxycarbonyl chloride 2.1 ngL- 15.2 ng L High sensitivity. Automated process. [55]... 

The C-4 acids (183 and 184) have also been subjected to borane reduction conditions to afford alcohol 195 in 23-50% yield or 64% yield as the C-8 epimeric mixture (195 and 196, Scheme 29) [34, 49, 64]. The C-8 alcohol epimers 195 and 196 have been treated separately as a common intermediate for a number of C-4 derivatives including esters, ethers, and amines [34, 49, 64], Alcohols 195 and 196 was subjected to DCC, DMAP, and desired acid chloride or carboxylic acid in CH2CI2 affording ester analogs in 50-92% yield [64], Esters prepared include alkyl, aryl, and fluorenylmethyloxycarbonyl (Fmoc) protected amino acid derivatives (197 and 198) [64]. Ethers were prepared with various alkyl halides and Ag20 in CH3CN at 40 °C. Alkyl, allyl, and benzyl ethers were prepared in 45-80% yield (199 and 200) [34,64]. Alcohols 195 and 196 were then activated to the triflates and displaced by a variety of amines by treatment with trifluoromethanesulfonic anhydride and desired amine in 22% - quantitative yield over two steps (201 and 202)... 

Amino groups are often protected as their terf-butyloxycarbonyl amide (Boc) or fluorenylmethyloxycarbonyl amide (Fmoc) derivatives. The Boc protecting group is introduced by reaction of the amino acid with di-fi rt-butyl dicarbonate in a nucleophilic acyl substitution reaction and is removed by brief treatment with a strong acid such as trifluoroacetic acid, CF3CO2H. The Fmoc protecting group is introduced by reaction with an acid chloride and is removed by treatment with base. 

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