159848-76-7

Upstream product

• 131791-82-7 3-amino-3-(4-methoxyphenyl)propionic acid methyl ester 
• 67-56-1 methanol 
• 131690-56-7 (S)-β-amino-β-(4-methoxyphenyl)propionic acid 
• 159990-11-1 (R)-2-tert-butoxycarbonylamino-1-methanesulfonyloxy-2-(4-methoxyphenyl)ethane 
• 193073-85-7 methyl (R)-2-((tert-butoxycarbonyl)amino)-2-(4-methoxyphenyl)acetate 
• 159990-12-2 (S)-3-tert-Butoxycarbonylamino-3-(4-methoxy-phenyl)-propionic acid 
• 159848-75-6 (S)-3-(N-terc-butoxycarbonylamine)-3-(4-methoxyphenyl)propanenitrile 
• 159848-74-5 1,1-dimethylethyl (R)-N-[2-hydroxy-1-(4-methoxyphenyl)-ethyl]carbamate 
• 5678-45-5 3-amino-3-(4-methoxyphenyl)propionic acid 
• 22027-50-5 methyl 3-(4-methoxybenzoyl)acetate 
• 96363-21-2 methyl (S)-3-tert-butoxycarbonylamino-3-(4-methoxyphenyl)propionate 

Downstream Products

• 1246195-65-2 C₁₄H₁₉NO₅ 
• 159848-85-8 (3S,3'S)-3--3-(4-methoxyphenyl)-1-(2,2,2-trichloroethoxycarbonyloxy)propane 
• 159848-97-2 (3S,3S')-3--3-(4-methoxyphenyl)-1-(2,2,2-trichloroethoxycarbonyloxy)propane 
• 159848-87-0 (3S,3'S)-3-<3'-acetoxy-N-tert-butoxycarbonyl-3'-(4-methoxyphenyl)propylamino>-3-(4-methoxyphenyl)-1-(2,2,2-trichloroethoxycarbonyloxy)propane 
• 159848-95-0 methyl (3S,3S')-3--3-(4-methoxyphenyl)propionate 
• 159848-86-9 (3S,3'S)-3--3-(4-methoxyphenyl)-1-(2,2,2-trichloroethoxycarbonyloxy)propane 
• 159848-83-6 methyl (3S,3'S)-3--3-(4-methoxyphenyl)propionate 
• 159848-96-1 (3S,3S')-3--3-(4-methoxyphenyl)-1-propanol 
• 159848-84-7 [(S)-3-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-phenyl)-propyl]-[(S)-3-hydroxy-1-(4-methoxy-phenyl)-propyl]-carbamic acid tert-butyl ester 
• 233274-73-2 3-(4-methoxy-phenyl)-3-[2-((3-methoxy-propyl)-{[4-(3-o-tolyl-ureido)-phenyl]-acetyl}-amino)-acetylamino]-propionic acid methyl ester 
• 233274-72-1 (S)-3-(4-Methoxy-phenyl)-3-[2-(3-methoxy-propylamino)-acetylamino]-propionic acid methyl ester 
• 444119-33-9 methyl (-)-(S)-3-(4-methoxyphenyl)-3-({3-[(4-methylphenylsulfonyl)amino]propyl}amino)propanoate 
• 233274-71-0 (S)-3-(2-Bromo-acetylamino)-3-(4-methoxy-phenyl)-propionic acid methyl ester 
• 159848-94-9 methyl (3S,3S')-3-<3'-tert-butoxycarbonylamino-3'-(4-methoxyphenyl)propylamino>-3-(4-methoxyphenyl)propionate 

Relevant academic research and scientific papers

Practical, catalytic enantioselective hydrogenation to synthesize N -unprotected β-amino esters

Practical and simple catalytic enantioselective hydrogenation reactions to synthesize N-unprotected β-amino esters have been developed: (1) asymmetric hydrogenation of N-unprotected β-enamine ester and (2) asymmetric direct reductive amination of β-keto esters using ammonium salts. A Ru-DM-SEGPHOS complex was used as the catalyst in both cases and gave high enantioselectivity, high reactivity, and wide substrate applicability. These protocols greatly reduced reaction time and waste compared to conventional synthetic routes. The direct reductive amination route was demonstrated on a >100 kg scale.

Stereoselective chemoenzymatic preparation of β-amino esters: Molecular modelling considerations in lipase-mediated processes and application to the synthesis of (S)-dapoxetine

A wide range of optically active 3-amino-3-arylpropanoic acid derivatives have been prepared by means of a stereoselective chemoenzymatic route. The key step is the kinetic resolution of the corresponding β-amino esters. Although the enzymatic acylations of the amino group with ethyl methoxyacetate showed synthetically useful enantioselectivities, the hydrolyses of the ester group catalyzed by lipase from Pseudomonas cepacia have been identified as the optimal processes concerning both activity and enantioselectivity. The enantiopreference of this lipase in these reactions has been explained, at the molecular level, by using a fragment-based approach in which the most favoured binding site for a phenyl ring and the most stable conformation of the 3-aminopropanoate core nicely match the (S)-configuration of the major products. The conversion and enantioselectivity values of the enzymatic reactions have been compared in order to understand the influence of the different substitution patterns present in the phenyl ring. This chemoenzymatic route has been successfully applied to the preparation of a valuable intermediate in the synthesis of (S)-dapoxetine, which has been chemically synthesised in excellent optical purity.

PROCESS FOR THE PREPARATION OF ENANTIOMERICALLY ENRICHED BETA AMINO ACID DERIVATIVES

The present invention relates to a process for the efficient preparation of enantiomerically enriched beta amino acid derivatives wherein the amino group is unprotected. The product chiral beta amino acid derivatives are useful in the asymmetric synthesis of biologically active molecules. The process comprises an enantioselective hydrogenation of an amine-unprotected prochiral beta-amino acrylic acid or derivative thereof in the presence of a rhodium metal precursor complexed with a chiral mono- or bisphosphine ligand.

Highly efficient synthesis of β-amino acid derivatives via asymmetric hydrogenation of unprotected enamines

A direct asymmetric hydrogenation of unprotected enamino esters and amides is described. Catalyzed by Rh complexes with Josiphos-type chiral ligands, this method gives β-amino esters and amides in high yield and high ee (93-97% ee). No acyl protection/deprotection is required. Copyright

Asymmetric syntheses of the macrocyclic spermine alkaloids (-)-(S)-protoverbine, (-)-(S)-buchnerine, and their naturally occurring congenial alkaloids

Asymmetric syntheses of the following 17-membered macrocyclic spermine alkaloids are presented: (-)-(S)-protoverbine (= (8S)-8-phenyl-1,5,9,13-tetraazacycloheptadecane-6-one: 1), (+)-(S)-protomethine (=(2S)-2-phenyl-1,5,9,14-tetraazabicyclo[12.3.1]octadec

Synthesis of enantiopure N-protected 4,5-disubstituted 3-pyrrolidinones and N-protected 2,5-disubstituted 3-pyrrolidinones via the Dieckmann reaction of dicarbonyl compounds derived from enantiopure β-amino esters

Under the action of KHMDS in THF solvent the Dieckmann reaction of dicarbonyl compounds derived from enantiopure β-amino esters provides enantiopure N-protected 4,5-disubstituted 3-pyrrolidinones, whereas N-protected 2,5-disubstituted 3-pyrrolidinones formed in reactions mediated by tert-BuOK in DMF or toluene. Reduction of these pyrrolidinones afforded enantiopure polysubstituted pyrrolidines.

Enantioselective acylation of β-aminoesters using penicillin G acylase in organic solvents

The resolution of racemic β-aminoesters has been achieved through selective acylation catalyzed by Penicillin G Acylase (ChiroCLEC(TM)-EC). The method has been optimized using three different phenylacetyl donors, and the effect of solvents on the rate of reaction is described. The efficiency of our method is illustrated by the synthesis of five different β-aminoesters with high enantiomeric purities.

Total Synthesis of 2'-Deoxymugineic Acid and Nicotianamine

Steroselective total synthesis of the unique phytosiderophores, 2'-deoxymugineic acid (4) and nicotianamine (5), has been achieved from the β-tyrosine derivative 21 using its aryl groups as the carboxyl synthon.