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ChemicalBook CAS DataBase List N-FMoc-L-norvaline
135112-28-6

N-FMoc-L-norvaline synthesis

3synthesis methods
-

Yield:-

Reaction Conditions:

Stage #1: L-Norvalinewith sodium carbonate in 1,4-dioxane;water;Cooling with ice;
Stage #2: (fluorenylmethoxy)carbonyl chloride in 1,4-dioxane;water at 20; for 5 h;

Steps:



General procedure: The N-FMOC derivatizedracemic and L-amino acids and methyl esters were preparedaccording to conventional methods.22 Racemic or L-α-amino acid (5 mmol) was dissolved in 10% aqueoussodium carbonate solution (12.5 mmol). Dioxane (7.5 mL)was then added and the mixture was stirred in an ice-bath.After that, 9-FMOC chloride (5 mmol) was added slowlyand stirred at room temperature for 5 h. Now, the reactionmixture was poured into water and extracted with ether.The aqueous solution obtained was acidified with c-HCl inan ice-bath. Finally, the resulting N-FMOC α-amino acidwas filtered and dried under vacuum. In order to prepareracemic or L-FMOC α-amino acid methyl ester, the correspondingFMOC α-amino acid (1 mmol) synthesized in theprevious step was dissolved in 5 mL of anhydrous methanolwith N,N0-dicyclohexylcarbodiimide (1.1 mmol). Themixture was stirred at room temperature for 12 h, filteredand dried under vacuum to get N-FMOC α-amino acidmethyl ester.

References:

Islam, Md. Fokhrul;Adhikari, Suraj;Paik, Man-Jeong;Lee, Wonjae [Bulletin of the Korean Chemical Society,2019,vol. 40,# 4,p. 332 - 338]

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