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The 50 mg of <strong>[22600-30-2]methyl 5-amino-2-furoate</strong>, 202 mg of N-Cbz-N-Boc-lysine, 123 ul of DIEA, and 202 mg of HBTU were dissolved in 1.5 ml DMF. After stirring at RT for 48 hours, the reaction was quenched by addition of 0.5 ml of water and diluted with 40 ml of EtOAc. The organic layer was washed with 1N HCl and brine, and worked-up as described in General Procedure. Pure title compound (1D) was obtained by purification on a fresh silica gel column eluted with 30% EtOAc in Hexane (56 mg, 31%).
Ethyl 2-amino-4-methyl thiazole-5-carboxylate (500 mg), 1.5 grams of N-Cbz-N-Boc-lysine, 0.99 ml of DIEA, and 2.0 grams of HBTU were dissolved in 15 ml DMF. After stirring at RT for 48 hours, the reaction was quenched by addition of 0.5 ml of water and diluted with 40 ml of EtOAc. The organic layer was washed with 1N HCl, brine and worked-up as described in General Procedure. Pure title compound (1C) was obtained by purification on a fresh silica gel column eluted with 30% EtOAc in Hexane (1.3 grams, 88%).
ethyl (R)-4-(2-(((benzyloxy)carbonyl)amino)-6-((tertbutoxycarbonyl)amino)hexanamido)-1-methyl-1H-imidazole-2-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
79%
With 5-nitro-2-(2-(pyridin-2-yl)propan-2-yl)benzo[d]isothiazol-3(2H)-one; CuI2(NMI)4; oxygen; triethyl phosphite; In acetonitrile; at 50℃; for 24h;Molecular sieve;
Figure ID shows a table of products produced by using a catalytic redox system comprising 20 mol % organocatalyst lg and 10 mol % CuI2(NMI)4 in MeCN under dry air (4 A molecular sieves) at 50 C, a variety of amides were constructed from 1.0 equiv of a carboxylic acid, 1.2 equiv of an amine, and 1.5 equiv of triethyl phosphite. For workup and isolation, the MeCN was filtered, and the solids were washed with CH2C12. The solvents were evaporated, and the products were obtained by Si02 chromatography. The entries span 1 and 2 amines, aliphatic and aromatic amines, amino acids and amino alcohols/phenols. The method is compatible with oxidation-prone substrates such as alkenes, boron derivatives, and furans and indoles as well as with electron-deficient heterocycles and benzene derivatives, and it works well for amines with a significant range of piH), chiral amine partners, chiral acid partners, and others. No racemization of stereocenters was observed for those substrates studied. The synthesis of peptide 3a shown in was carried out on a 5 g scale and delivered the product in 91% yield after 24 h at 50 C.
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