135865-78-0

Basic information

• Product Name: (S)-tert-butyl 3-oxo-1-phenylpropylcarbamate
• Synonyms: (S)-tert-butyl 3-oxo-1-phenylpropylcarbamate;N-Boc-(3S)-3-phenyl-3-aminopropionaldehyde;Maraviroc Intermediate 3;Maraviroc interMediate(aMino acid);tert-butyl 2-aMino-4-oxo-2-phenylbutanoate;N-[(1S)-3-Oxo-1-phenylpropyl]-;(S)-tert-Butyl 3-oxo-1-phenylpropylcarbaMate (Maraviroc InterMediates);CarbaMic acid,N-[(1S)-3-oxo-1-phenylpropyl]-, 1,1-diMethylethyl ester
• CAS NO: 135865-78-0
• Molecular Formula: C₁₄H₁₉NO₃
• Molecular Weight: 249.31
• Product Categories: Amines;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 135865-78-0.mol
• Article Data: 35

Chemical Properties

• Boiling Point: 371.9 °C at 760 mmHg
• Flash Point: 178.7 °C
• Appearance: /
• Density: 1.075 g/cm³
• Vapor Pressure: 9.96E-06mmHg at 25°C
• Refractive Index: 1.508
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility: Chloroform, DMSO, Ethyl Acetate, Methanol
• PKA: 11.56±0.46(Predicted)
• CAS DataBase Reference: (S)-tert-butyl 3-oxo-1-phenylpropylcarbamate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-tert-butyl 3-oxo-1-phenylpropylcarbamate(135865-78-0)
• EPA Substance Registry System: (S)-tert-butyl 3-oxo-1-phenylpropylcarbamate(135865-78-0)

Safety Data

• Hazardous Substances Data: 135865-78-0(Hazardous Substances Data)

Usage

Description

(S)-tert-butyl 3-oxo-1-phenylpropylcarbamate is an organic compound characterized as a white solid. It is a crucial intermediate in the synthesis of spirotropane compounds, which are known for their role in modulating CCR5 chemokine receptors.

Uses

Used in Pharmaceutical Industry:
(S)-tert-butyl 3-oxo-1-phenylpropylcarbamate is used as a key intermediate for the preparation of spirotropane compounds. These compounds serve as modulators of CCR5 chemokine receptors, which are involved in various biological processes and have potential therapeutic applications in treating diseases such as HIV, certain cancers, and inflammatory conditions.
The compound's role as an intermediate in the synthesis of spirotropane compounds highlights its importance in the development of new drugs targeting CCR5 chemokine receptors, making it a valuable asset in the pharmaceutical industry.

InChI:InChI=1/C14H19NO3/c1-14(2,3)18-13(17)15-12(9-10-16)11-7-5-4-6-8-11/h4-8,10,12H,9H2,1-3H3,(H,15,17)/t12-/m0/s1

Upstream product

• 126568-44-3 (S)-3-(N-tert-butoxycarbonylamino)-3-phenylpropanenitrile 
• 167834-23-3 ethyl (3S)-3-{[(tert-butoxy)carbonyl]amino}-3-phenylpropanoate 
• 75-07-0 acetaldehyde 
• 150884-50-7 benzaldehyde N-boc imine 
• 934237-45-3 tert-butyl (3S,5S)-5-hydroxy-3-phenylisoxazolidine-2-carboxylate 
• 100-52-7 benzaldehyde 
• 3646-50-2 3-Amino-3-phenylpropionic acid 
• 622830-41-5 (+/-)-β-phenylalanine propyl ester 
• 82769-76-4 (S)-3-amino-3-phenylpropanol 
• 103365-47-5 (S)-3-(tert-butoxycarbonylamino)-3-phenylpropanoic acid 
• 1624-53-9 2-(benzylideneamino)phenol 
• 1014702-81-8 (5-benzyl-hexahydro-pyrrolo[3,4-c]pyrrol-2-yl)-(4,6-dimethyl-pyrimidin-5-yl)-methanone 
• 24424-99-5 di-tert-butyl dicarbonate 
• 37088-66-7 (3S)-methyl 3-amino-3-phenylpropanoate 

Downstream Products

• 957122-37-1 methyl 1-({(3S)-3-[(tert-butoxycarbonyl)amino]-3-phenylpropyl}amino)cyclopentanecarboxylate 
• 718611-17-7 S-(3-hydroxy-1-phenyl-propyl)-carbamic acid tert-butyl ester 
• 718611-16-6 C₂₈H₄₀N₂O₆S₂ 
• 478408-20-7 tert-butyl-(1S)-1-phenyl-3-(4-[3-benzyl-1-ethyl(1H-pyrazol-5-yl)]piperidin-1-yl)propylcarbamate 
• 872001-34-8 C₂₇H₃₇N₃O₂ 
• 1014702-73-8 C₃₀H₄₁N₅O₃ 
• 1014702-90-9 C₂₉H₃₉N₅O₃ 
• 1014702-96-5 C₃₂H₄₄FN₅O₃ 
• 1014702-57-8 3-{3-[5-(4,6-dimethyl-pyrimidine-5-carbonyl)-hexahydro-pyrrolo[3,4-c]pyrrol-2-yl]-1-phenyl-propyl}-azetidine-1-carboxylic acid tert-butyl ester 
• 1014703-35-5 C₃₂H₄₄FN₅O₃ 
• 1014703-40-2 C₃₃H₄₆FN₅O₃ 
• 1114997-31-7 C₂₂H₃₁N₅O₂ 
• 1114997-40-8 C₂₇H₃₄N₄O₂ 

Relevant articles and documents

Concise enantioselective synthesis of (+)-sertraline and (-)-CP-52002 using proline catalysis

A short enantioselective synthesis of (+)-sertraline and its C4 epimer (-)-CP-52002 with an overall yield of 30%, respectively, as its hydrochloride has been described. The key steps are the proline catalyzed Mannich reaction of acetaldehyde and acid catalyzed intramolecular Friedel-Crafts' alkylation reaction of olefin proceeding with high optical purities.

Chiral Bronsted acid-catalyzed tandem aza-ene type reaction/cyclization cascade for a one-pot entry to enantioenriched piperidines

A chiral monophosphoric acid-catalyzed tandem aza-ene type reaction/cyclization cascade enabled the rapid construction of enantioenriched piperidine derivatives as key structural elements of numerous natural products. The potential of such cascade transformations is highlighted through their ability to achieve a rapid increase in molecular complexity from simple enecarbamates and a broad range of aldimines while also controlling three stereogenic centers in a highly diastereo- and enantioselective manner. Copyright

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.

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.