19317-12-5

Upstream product

• 15196-02-8 (S)-3-[(benzyloxycarbonyl)amino]-1-diazo-4-phenyl-2-butanone 
• 35909-92-3 N-carbobenzoxy-L-phenylalanine methyl ester 
• 41518-17-6 Z-Phe-O-COO-isoBu 
• 1161-13-3 N-Cbz-L-Phe 
• 143601-45-0 (S)-tert-butyl 4-<(benzyloxycarbonyl)amino>-3-oxo-5-phenylpentanoate 
• 109453-49-8 (C₈H₇O₂)(NHCHCOO)(CH₂C₆H₅)(CO₂C₂H₅) 
• 191226-91-2 4-benzyloxycarbonylamino-2-bromo-3-oxo-5-phenyl-pentanoic acid tert-butyl ester 

Downstream Products

• 128018-44-0 N-benzyloxycarbonyl-3(S)-amino-1,2(S)epoxy-4-phenylbutane 
• 198020-19-8 (2R,2S)-(3S)-1,2-epoxy-3-phenylmethoxycarbonylamino-4-phenylbutane 
• 269085-45-2 benzyl (S)-1-(1H-imidazol-4-yl)-2-phenylethylcarbamate 
• 852248-39-6 2-phenyl-4-(1-(S)-amino-2-phenylethyl)-1H-imidazole 
• 118388-01-5 (S)-2-Benzyl-5-benzyloxycarbonylamino-4-oxo-6-phenyl-hexanoic acid 
• 118388-00-4 2-Benzyl-2-((S)-3-benzyloxycarbonylamino-2-oxo-4-phenyl-butyl)-malonic acid 
• 124267-01-2 ((S)-1-Benzyl-4-{(S)-1-[(S)-2-((S)-1-benzylcarbamoyl-3-methyl-butylcarbamoyl)-1-hydroxy-ethyl]-3-methyl-butylcarbamoyl}-2-hydroxy-5-phenyl-pentyl)-carbamic acid benzyl ester 
• 118405-21-3 ((S)-1-Benzyl-4-{(S)-1-[(S)-2-((S)-1-benzylcarbamoyl-3-methyl-butylcarbamoyl)-1-hydroxy-ethyl]-3-methyl-butylcarbamoyl}-2-oxo-5-phenyl-pentyl)-carbamic acid benzyl ester 
• 1243276-83-6 benzyl 1-(2-amino-1,3-selenazol-4-yl)-2-phenylethylcarbamate 
• 269085-42-9 2-phenyl-4-(1-(S)-benzyloxycarbonylamino-2-phenylethyl)-1H-imidazole 
• 128017-85-6 N-[[N-(benzyloxycarbonyl)-L-phenylalanyl]methyl]-L-proline tert-butyl ester 
• 191226-93-4 (3S)-3-(N-benzyloxycarbonyl)amino-3-benzyl-2-hydroxy-1-bromopropane 
• 120452-06-4 3(S)-(Benzyloxyformamido)-1-bromo-4-phenyl-2(S)-butanol 

Relevant academic research and scientific papers

Continuous flow synthesis of α-halo ketones: Essential building blocks of antiretroviral agents

The development of a continuous flow process for the multistep synthesis of α-halo ketones starting from N-protected amino acids is described. The obtained α-halo ketones are chiral building blocks for the synthesis of HIV protease inhibitors, such as atazanavir and darunavir. The synthesis starts with the formation of a mixed anhydride in a first tubular reactor. The anhydride is subsequently combined with anhydrous diazomethane in a tube-in-tube reactor. The tube-in-tube reactor consists of an inner tube, made from a gas-permeable, hydrophobic material, enclosed in a thick-walled, impermeable outer tube. Diazomethane is generated in the inner tube in an aqueous medium, and anhydrous diazomethane subsequently diffuses through the permeable membrane into the outer chamber. The α-diazo ketone is produced from the mixed anhydride and diazomethane in the outer chamber, and the resulting diazo ketone is finally converted to the halo ketone with anhydrous ethereal hydrogen halide. This method eliminates the need to store, transport, or handle diazomethane and produces α-halo ketone building blocks in a multistep system without racemization in excellent yields. A fully continuous process allowed the synthesis of 1.84 g of α-chloro ketone from the respective N-protected amino acid within ～4.5 h (87% yield).

One-pot synthesis of orthogonally protected dipeptide selenazoles employing Nα-amino selenocarboxamides and α-bromomethyl ketones

A simple and efficient protocol for the synthesis of selenazole containing dipeptidomimetics using Nα-amino selenocarboxamides and α-bromomethyl ketones is described. All the compounds made were isolated in good yields and fully characterized.

Ultrasound mediated synthesis of 2-amino-1,3-selenazoles derived from Fmoc/Boc/Z-α-amino acids

A simple and efficient one-pot synthesis of Fmoc/Boc/Z-amino acid derived 2-amino-1,3-selenazoles by the condensation of Nα-urethane protected amino acid derived bromomethyl ketones with selenourea under the influence of ultrasound has been described. Insertion of 2-amino-1,3-selenazole moiety in the side chains of Asp and Glu has also been achieved following the similar protocol. ARKAT USA, Inc.

Facile synthesis of optically active imidazole derivatives

Five optically active imidazole derivatives have been synthesized via a facile 4-step reaction sequence starting from commercially available and inexpensive N-Cbz amino acids. While microwave assisted condensation was unsuccessful, the condensation of the

Chiral imidazole derivatives synthesis from enantiopure N-protected α-amino acids

A route to the preparation of enantiopure ligands based on a 2-phenylimidazol ring is described. The stereogenic centre is placed into the chain bonded to the fourth carbon of the imidazole ring. The synthesis starts from inexpensive and readily available

Synthesis of optically active α-aminoalkyl α′-halomethyl ketone: A cross-claisen condensation approach

(Equation presented) A simple and versatile method was developed for the synthesis of α-aminoalkyl α′-halomethyl ketone derivatives, which are useful intermediates of protease inhibitors. It involves selective halogenation of the α-position on a β-ketoester, which is prepared by cross-Claisen condensation using N-protected amino acid ester. The title compound is obtained in high yield after decarboxylation of the α-halo-β-ketoester.

Highly stereoselective synthesis of anti-N-protected-α-amino epoxides

A simple and efficient method for the synthesis of anti-N-protected amino epoxides from carbamate-protected amino acids is described. The two key steps are the monobromination of a β-ketoester and chelation-controlled reduction of a bromomethyl ketone intermediate. Good overall yields, high diastereoselectivity, and excellent functional group compatibility are characteristic.

Process for producing 3-amino-2-oxo-1-halogenopropane derivatives

Compounds formed by reacting a protected amino acid with an alkali metal enolate of an alkyl acetate are reacted with a halogenating agent for halogenation of the 2-position, or a protected amino acid is reacted with an alkali metal enolate of an alkyl halogenoacetate, to form a 4-amino-3-oxo-2-halogenobutanoic acid ester derivative, and hydrolysis and decarboxylation are conducted to produce a 3-amino-2-oxo-1-halogenopropane derivative or its salt. The present method is a useful process for producing a 3-amino-2-oxo-1-halogenopropane derivatives which can easily be converted to a 3-amino-1,2-epoxypropane.

Synthesis of N-protection erythro-phenylalanylepoxides

The synthesis of erythro-isomers of N-α-t-Boc, N-α-Fmoc- and N-α-Cbz-L-phenylalanylepoxides from the appropriate N-α-protected L-phenylalanines via bromomethyl-ketone intermediates is described.

Stereocontrolled synthesis of erythro N-protected α-amino epoxides and peptidyl epoxides

N-protected α-amino epoxides of erythro configuration, derived from α-amino acids, were synthesized in a stereoselective manner. The erythro (2S,3S), configuration was achieved by the synthetic sequence: amino acid -> haloketone -> halohydrin -> epoxide. A mechanistic explanation for the observed stereoselectivity is presented. This stereoselective synthetic approach was applied to the synthesis of a variety of short peptidyl epoxides, bearing a predefined absolute configuration of the chiral epoxide moiety.