718611-17-7

Usage

Uses

Used in Organic Synthesis:
(S)-N-BOC-3-AMINO-3-PHENYL-PROPAN-1-OL is used as a building block in organic synthesis for the preparation of pharmaceuticals, agrochemicals, and other fine chemicals. Its unique structure and BOC-protected amine group make it a valuable intermediate in the synthesis of complex organic molecules.
Used in Medicinal Chemistry and Drug Discovery:
(S)-N-BOC-3-AMINO-3-PHENYL-PROPAN-1-OL is used as a potential candidate in medicinal chemistry and drug discovery due to its potential biological activity. Its unique structure and functional groups may contribute to the development of new therapeutic agents with novel mechanisms of action.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (S)-N-BOC-3-AMINO-3-PHENYL-PROPAN-1-OL is used as a key intermediate in the synthesis of various drug molecules. Its BOC-protected amine group allows for selective transformations, facilitating the development of new drugs with improved efficacy and safety profiles.
Used in Agrochemical Industry:
(S)-N-BOC-3-AMINO-3-PHENYL-PROPAN-1-OL is used as a building block in the agrochemical industry for the synthesis of various agrochemicals, such as pesticides and herbicides. Its unique structure and functional groups may contribute to the development of new agrochemicals with enhanced performance and selectivity.

Upstream product

• 103365-47-5 (S)-3-(tert-butoxycarbonylamino)-3-phenylpropanoic acid 
• 135865-78-0 tert-butyl (1S)-3-oxo-1-phenylpropylcarbamate 
• 1067647-06-6 (S)-2-oxo-4-phenyl-azetidine-1-carboxylic acid tert-butyl ester 
• 374725-03-8 tert-butyl (-formyl-1-phenylethyl)carbamate 
• 765922-42-7 (S)-propyl 3-amino-3-phenylpropanoate 
• 155396-71-7 tert-butyl N-(phenyl(phenylsulfonyl)methyl)carbamate 
• 4248-19-5 tert-butyl carbazate 
• 1624-53-9 2-(benzylideneamino)phenol 
• 100-52-7 benzaldehyde 
• 24424-99-5 di-tert-butyl dicarbonate 
• 150884-50-7 benzaldehyde N-boc imine 
• 622830-41-5 (+/-)-β-phenylalanine propyl ester 
• 3646-50-2 3-Amino-3-phenylpropionic acid 
• 146924-91-6 (-)-cis-(3S,4R)-3-hydroxy-1-(4-methoxyphenyl)-4-phenyl-2-azetidinone 

Downstream Products

• 1398626-52-2 (S)-4-amino-4-phenylbutyric acid sodium salt 
• 1398626-55-5 ((S)-3-cyano-1-phenylpropyl)carbamic acid tert-butyl ester 
• 949096-34-8 (S)-4-amino-4-phenylbutan-1-ol 
• 1150560-58-9 methanesulfonic acid (S)-3-tert-butoxycarbonylamino-3-phenylpropyl ester 
• 1630982-20-5 (S)-tert-butyl (3-amino-1-phenylpropyl)carbamate 
• 376348-70-8 tert-butyl (1S)-3-[3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-exo-8-azabicyclo[3.2.1]oct-8-yl]-1-phenylpropylcarbamate 
• 376348-71-9 (S)-3-((1R,3R,5S)-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl)-1-phenylpropan-1-amine 
• 376348-65-1 maraviroc 
• 82769-76-4 (S)-3-amino-3-phenylpropanol 
• 103365-47-5 (S)-3-(tert-butoxycarbonylamino)-3-phenylpropanoic acid 
• 718611-16-6 C₂₈H₄₀N₂O₆S₂ 

Relevant academic research and scientific papers

Synthesis method of dapoxetine impurities

The invention provides a synthesis method of dapoxetine impurities, which comprises the following synthesis steps of: reacting (S)-3-amino-3-phenyl propanol with Boc anhydride to obtain a compound B; reducing the compound B under the action of a reducing agent to obtain a dapoxetine impurity 1; reacting the impurity 1 with 1-fluoronaphthalene under the action of alkali to obtain an impurity 2; and reacting the impurity 2 with chloroformate to obtain an impurity 3. According to the synthesis method of the dapoxetine impurities, the three dapoxetine impurities can be obtained in sequence, the starting raw materials are wide in source, the cost is low, the synthesis steps are short, all the steps are conventional experiment operation, special reagents or toxic reagents do not need to be used, and the prepared dapoxetine impurity products are high in purity and do not need tedious purification operation. The synthesized three impurities are applied to dapoxetine hydrochloride quality control, are helpful for perfecting the quality standard of dapoxetine hydrochloride, and have important meanings for improving the quality of dapoxetine hydrochloride raw material medicines and preparations thereof and the medication safety.

Synthetic method of dapoxetine and intermediate thereof

The invention discloses a synthetic method of dapoxetine and its intermediate, i.e., (S)-3-(tert-butyloxycarbonyl)amino-3-phenylpropanol as shown in a formula 5 which is described in the specification. The synthetic method of (S)-3-(tert-butyloxycarbonyl)amino-3-phenylpropanol is as shown in a synthesis route which is described in the specification, wherein a compound 3 and acetaldehyde are subjected to a Mannich reaction in an organic solvent under the action of a supramolecular catalyst constructed by a chiral catalyst and a polymer so as to obtain a compound 4, and the polymer is at least one selected from of the group consisting of PEG 200, PEG 400, PEG 600, MeOPEG 750, PEG 800, PEG 1000, PPG 800 and PPG 1000. The dapoxetine is synthesized from the (S)-3-(tert-butyloxycarbonyl)amino-3-phenylpropanol prepared by using the above method according to steps as shown in the synthesis route. The synthetic method of dapoxetine and the intermediate thereof has the characteristics of usage of cheap and easily available raw materials, high yield and low cost, and is more beneficial to industrial production.

Chiral N,N′-Dioxide/Tm(OTf)3 Complex-Catalyzed Asymmetric Bisvinylogous Mannich Reaction of Silyl Ketene Acetal with Aldimines

An enantioselective bisvinylogous Mannich reaction of silyl ketene acetal with aldimines has been realized by using a chiral N,N′-dioxide/Tm(OTf)3 complex as catalyst, providing an effective method to synthesize chiral ζ-amino-α,β,γ,δ-unsaturated carbonyl compounds. (Figure presented.).

Configurationally Stable (S)- and (R)-α-Methylproline-Derived Ligands for the Direct Chemical Resolution of Free Unprotected β3-Amino Acids

Reported herein is a chemical method for the direct resolution of unprotected racemic β-substituted-β-amino acids (β3-AAs) that uses specially designed, stable, and recyclable α-methylproline-derived chiral ligands. The versatility of this methodology is unmatched by biocatalytic approaches. The method shows a broad synthetic generality for various aryl- or alkyl-substituted β3-AAs, and the new nonracemizable ligands can be accessed readily. Furthermore, the presented method produces an excellent stereochemical outcome and has a fully recyclable source of chirality, and the reaction conditions are operationally simple and convenient. The procedure has also been successfully applied to the scalable synthesis of the anti-HIV drug maraviroc.

Synthetic method for novel chiral ligand, metal chelate, multiple unnatural amino acids, maraviroc and key intermediate thereof

The invention discloses a synthetic method for a novel chiral ligand, a metal chelate, multiple unnatural amino acids, maraviroc and a key intermediate thereof. According to the synthetic method, (R)-2-methylproline is selected as a starting material, and asymmetrical resolution is induced by utilizing a nickel chelate, so that (S)-beta3-amino acid is obtained, and (S)-3-amino-3-phenylpropionic acid is taken as the key intermediate for synthesizing maraviroc, so that yield is high, and ee value reaches more than or equal to 98.2%. The method disclosed by the invention has the advantages that source of raw materials is wide, conditions of a synthetic process are mild, control is easy, and optical purity of products is high.

Direct Asymmetric Vinylogous and Bisvinylogous Mannich-Type Reaction Catalyzed by a Copper(I) Complex

A direct catalytic asymmetric vinylogous Mannich-type reaction has been disclosed in good yield, excellent regio-, diastereo- and enantioselectivity. The key to control the regioselectivity is the combination of a bulky N-acylpyrazole and a bulky bisphosphine ligand. The catalytic system was extended to a bisvinylogous Mannich-type reaction by changing the ligand. The synthetic utility of the vinylogous products was demonstrated by several transformations.

A chiral analog of the bicyclic guanidine TBD: Synthesis, structure and Br?nsted base catalysis

Starting from (S)-β-phenylalanine, easily accessible by lipase-catalyzed kinetic resolution, a chiral triamine was assembled by a reductive amination and finally cyclized to form the title compound 10. In the crystals of the guanidinium benzoate salt the six membered rings of 10 adopt conformations close to an envelope with the phenyl substituents in pseudo-axial positions. The unprotonated guanidine 10 catalyzes Diels-Alder reactions of anthrones and maleimides (25-30% ee). It also promotes as a strong Br?nsted base the retro-aldol reaction of some cycloadducts with kinetic resolution of the enantiomers. In three cases, the retroaldol products (48-83% ee) could be recrystallized to high enantiopurity (≥95% ee). The absolute configuration of several compounds is supported by anomalous X-ray diffraction and by chemical correlation.

Process for preparation of enantiomerically pure S-(+)-N, N-dimethyl-a-[2-(naphthalenyloxy)ethyl] benzenemethanamine

The present invention relates to improved, efficient process for the preparation of enantiomerically pure S-(+)-N,N-dimethyl-a-[2-(naphthalenyloxy)ethyl] benzenemethanamine and pharmaceutically acid addition salts thereof. The present invention particularly provides a process for preparation of (3S, 4R)-3-hydroxy-1-(4-methoxyphenyl)-4-phenylazetidin-2-one useful as a key intermediate for preparation of (s)-dapoxetine.

BRANCHED OXATHIAZINE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF, USE THEREOF AS MEDICINE AND DRUG CONTAINING SAID DERIVATIVES AND USE THEREOF

The invention relates to compounds of formula (I) and to the physiologically compatible salts thereof. Said compounds are suitable, for example, for treating hyperglycemia.

Synthesis and in vitro sodium channel blocking activity evaluation of novel homochiral mexiletine analogs

New chiral mexiletine analogs were synthesized in their optically active forms and evaluated in vitro as use-dependent blockers of skeletal muscle sodium channels. Tests carried out on sodium currents of single muscle fibers of Rana esculenta demonstrated