103365-47-5

Basic information

• Product Name: (S)-N-Boc-3-Amino-3-phenylpropanoic acid
• Synonyms: RARECHEM AK PT B078;(S)-3-TERT-BUTOXYCARBONYLAMINO-3-PHENYL-PROPIONIC ACID;(S)-3-(BOC-AMINO)-3-PHENYLPROPIONIC ACID;(S)-N-(TERT-BUTOXYCARBONYL)-3-AMINO-3-PHENYLPROPIONIC ACID;(S)-N-BOC-BETA-PHENYL-BETA-ALANINE;(S)-N-BOC-3-AMINO-3-PHENYLPROPANOIC ACID;N-T-BUTOXYCARBONYL-(S)-3-AMINO-3-PHENYLPROPIONIC ACID;BOC-(S)-3-AMINO-3-PHENYLPROPIONIC ACID
• CAS NO: 103365-47-5
• Molecular Formula: C₁₄H₁₉NO₄
• Molecular Weight: 265.3
• Product Categories: 3-Amino-3-phenylpropionic Acid Analogs;3-Amino-3-phenylpropanoic Acid Analogs;API intermediates;B-Amino;Unusual Amino Acids - Phe
• Mol File: 103365-47-5.mol
• Article Data: 17

Chemical Properties

• Melting Point: 122.9 °C
• Boiling Point: 408.52°C (rough estimate)
• Flash Point: 209.8 °C
• Appearance: white chunks
• Density: 1.1356 (rough estimate)
• Vapor Pressure: 6.42E-08mmHg at 25°C
• Refractive Index: 1.5110 (estimate)
• Storage Temp.: 2-8°C
• PKA: 4.32±0.10(Predicted)
• CAS DataBase Reference: (S)-N-Boc-3-Amino-3-phenylpropanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-N-Boc-3-Amino-3-phenylpropanoic acid(103365-47-5)
• EPA Substance Registry System: (S)-N-Boc-3-Amino-3-phenylpropanoic acid(103365-47-5)

Safety Data

• Safety Statements: 24/25
• HazardClass: IRRITANT
• Hazardous Substances Data: 103365-47-5(Hazardous Substances Data)

Usage

Description

(S)-N-Boc-3-Amino-3-phenylpropanoic acid, also known as (S)-3-Phenyl-3-(tert-butoxycarbonylamino)propanoic acid, is an unnatural amino acid derivative characterized by its white chunky appearance. It is a chiral compound with the (S) configuration, which is crucial for its specific applications and interactions.

Uses

Used in Pharmaceutical Industry:
(S)-N-Boc-3-Amino-3-phenylpropanoic acid is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a versatile building block for the development of new drugs with potential therapeutic applications.
Used in the Synthesis of Carnosine:
(S)-N-Boc-3-Amino-3-phenylpropanoic acid is used as a precursor in the synthesis of Carnosine (C184190), a naturally occurring dipeptide with antioxidant and anti-glycating properties. Carnosine has been studied for its potential role in preventing neurodegenerative diseases and other health benefits.
Used as a Sequestering Agent:
(S)-N-Boc-3-Amino-3-phenylpropanoic acid and its derivatives are used as selective and efficient sequestering agents for cytotoxic reactive carbonyl species. This application is particularly relevant in the development of therapeutic agents that can protect cells from oxidative stress and related damage.

InChI:InChI=1/C14H19NO4/c1-14(2,3)19-13(18)15-11(9-12(16)17)10-7-5-4-6-8-10/h4-8,11H,9H2,1-3H3,(H,15,18)(H,16,17)/p-1/t11-/m0/s1

Upstream product

• 614-19-7 (S)-3-amino-3-phenylpropanoic acid 
• 41840-28-2 S-tert-butoxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine 
• 126568-44-3 (S)-3-(N-tert-butoxycarbonylamino)-3-phenylpropanenitrile 
• 135865-77-9 (S)-N-(tert-Butoxycarbonyl)-1-phenyl-3-butenylamine 
• 718611-17-7 S-(3-hydroxy-1-phenyl-propyl)-carbamic acid tert-butyl ester 
• 124-38-9 carbon dioxide 
• 183990-25-2 ((R)-2-Chloro-1-phenyl-ethyl)-carbamic acid tert-butyl ester 
• 190189-97-0 methyl (3S)-3-[(tert-butoxycarbonyl)amino]-3-phenylpropionate 
• 885696-47-9 2-(tert-butoxycarbonylamino-phenyl-methyl)-malonic acid dimethyl ester 
• 890043-61-5 (S)-2-(tert-butoxycarbonylaminophenylmethyl)malonic acid dibenzyl ester 
• 177896-09-2 tert-butyl benzylidenecarbamate 
• 37088-66-7 (3S)-methyl 3-amino-3-phenylpropanoate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 56613-80-0 D-2-phenylglycinol 

Downstream Products

• 16857-27-5 (6R)-3-acetoxymethyl-7t-((S)-3-tert-butoxycarbonylamino-3-phenyl-propionylamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 190189-97-0 methyl (3S)-3-[(tert-butoxycarbonyl)amino]-3-phenylpropionate 
• 107199-64-4 Benzoic acid 4-{benzoyl-[3-((S)-3-tert-butoxycarbonylamino-3-phenyl-propionylamino)-propyl]-amino}-butyl ester 
• 126568-48-7 Benzoic acid 3-{benzyl-[4-((S)-3-tert-butoxycarbonylamino-3-phenyl-propionylamino)-butyl]-amino}-propyl ester 
• 107199-59-7 3-Phenyl-propionic acid 4-[[3-((S)-3-tert-butoxycarbonylamino-3-phenyl-propionylamino)-propyl]-(3-phenyl-propionyl)-amino]-butyl ester 
• 184872-83-1 ((S)-2-{3-[4-(2-Chloro-ethyl)-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl]-propylcarbamoyl}-1-phenyl-ethyl)-carbamic acid tert-butyl ester 
• 718611-17-7 S-(3-hydroxy-1-phenyl-propyl)-carbamic acid tert-butyl ester 
• 220760-53-2 (S)-2-((S)-3-tert-Butoxycarbonylamino-3-phenyl-propionyloxy)-4-methyl-pentanoic acid allyl ester 
• 532393-80-9 (3S)-N-Boc-3-amino-β-phenylalanine-L-valine-(4S)-methylsuccinimide 
• 945979-05-5 Boc-(S)-β³-hPhg-D-Oxd-OBn 

Relevant articles and documents

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.

Ureidopeptide-based Bronsted bases: Design, synthesis and application to the catalytic enantioselective synthesis of β-amino nitriles from (arylsulfonyl)acetonitriles

The addition of cyanoalkyl moieties to imines is a very attractive method for the preparation of β-amino nitriles. We present a highly efficient organocatalytic methodology for the stereoselective synthesis of β-amino nitriles, in which the key to success is the use of ureidopeptide-based Bronsted base catalysts in combination with (arylsulfonyl)acetonitriles as synthetic equivalents of the acetonitrile anion. The method gives access to a variety of β-amino nitriles with good yields and excellent enantioselectivities, and broadens the stereoselective Mannich-type methodologies available for their synthesis. Learning from peptides: A concise route for the catalytic enantioselective synthesis of β-amino nitriles has been achieved by using ureidopeptide-based Bronsted bases as catalysts in the Mannich reaction of N-Boc imines and (arylsulfonyl)acetonitriles (see scheme; Boc=tert-butoxycarbonyl, napht=naphthyl, TMS=trimethylsilyl).

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