2899-58-3

Upstream product

• 524-38-9 N-hydroxyphthalimide 
• 1138-80-3 N-(Benzyloxycarbonyl)glycine 
• 91837-50-2 N-trichloroacetoxyphthalimide 

Downstream Products

• 13437-63-3 methyl [({[(benzyloxy)carbonyl]amino}acetyl)amino]acetate 
• 41888-85-1 N-(N-benzyloxycarbonyl-glycyl)-DL-phenylalanine methyl ester 
• 76476-13-6 O-(benzyloxycarbonylglycyl)-N-hydroxy-DL-alanine t-butyl ester 
• 138479-39-7 dimethyl 1-hydroxy-1-phenyl-2-N-(N'-benzoxycarbonylglycyl)-aminoethyl-phosphonate 
• 3227-12-1 N--funtumin 

Relevant academic research and scientific papers

Regioselective amidomethylation of 4-chloro-3-fluoropyridine by metalation and minisci-type reactions

The synthesis of a series of 2-amidomethylated pyridines (3-8) was investigated, starting from 4-chloro-3- fluoropyridine. Kinetic deprotonation at -75 °C followed by reaction with DMF gave 2-formyl-4-chloro-3-fluoropyridine 10 regioselectively, which was converted to 2-aminomethyl analogue 1 via sulfinamide 2. Alternatively, Minisci-type amidomethylation under Ag+/persulfate or photoredox-mediated conditions using a series of amino acid derivatives gave (3-8, 19, and 34) in 30-74% yield and isomer ratios in the range 6.7:1 to >50:1. The latter methods gave overall yields similar to that of the deprotonation approach, but were shorter and more amenable to scale-up. In particular, N-Boc analogue 8 was obtained in a single step. The amidomethylations of another six 3-fluoropyridines under the photoredox conditions were briefly examined.

Photocatalytic decarboxylative alkenylation of α-amino and α-hydroxy acid-derived redox active esters by NaI/PPh3 catalysis

Herein, we report the photocatalytic decarboxylative alkenylation reactions of N-(acyloxy)phthalimide derived from α-amino and α-hydroxy acids with 1,1-diarylethene, and with cinnamic acid derivatives through double decarboxylation, using sodium iodide and triphenylphosphine as redox catalysts. The reaction proceeds under mild irradiation conditions with visible blue light (440 nm or 456 nm) in an acetone solvent without recourse to transition-metal or organic dye based photoredox catalysts. The reaction proceeds via photoactivation of a transiently self-assembled chromophore from N-(acyloxy)phthalimide and NaI/PPh3. Solvation plays a crucial role in the reactivity.

Studies on organophosphorus compounds; LXXIII: Synthesis of phosphonopeptides by an in situ active ester method

An active ester prepared in situ from an N-protected amino acid and N-hydroxyphthalimide was successfully employed in the synthesis of phosphonopeptides bearing a free hydroxy group.