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

• 24424-99-5 di-tert-butyl dicarbonate 
• 150884-50-7 benzaldehyde N-boc imine 
• 3646-50-2 3-Amino-3-phenylpropionic acid 
• 100-52-7 benzaldehyde 
• 614-19-7 (S)-3-amino-3-phenylpropanoic acid 
• 591-51-5 phenyllithium 
• 126568-41-0 Benzyl-((1R,2S,3S)-4-benzyloxy-2,3-bis-methoxymethoxy-1-phenyl-butyl)-amine 
• 126568-43-2 Benzyl-((1R,2S,3S)-4-benzyloxy-2,3-dihydroxy-1-phenyl-butyl)-carbamic acid tert-butyl ester 
• 126610-77-3 (R)-tert-butyl N-<1-phenyl-2-<(p-toluenesulfonyl)oxy>ethyl>carbamate 
• 126568-42-1 (1R,2S,3S)-1-Benzylamino-4-benzyloxy-1-phenyl-butane-2,3-diol 
• 126610-76-2 Benzyl-((R)-2-hydroxy-1-phenyl-ethyl)-carbamic acid tert-butyl ester 
• 14231-57-3 (R)-N-benzyl-2-phenylglycinol 
• 956101-46-5 tert-butyl [(1S)-1-phenylprop-2-en-1-yl]imidocarbonate 
• 125414-45-1 (2R,3R)-3-<(tert-butoxycarbonyl)amino>-3-phenyl-1,2-propanediol 

Downstream Products

• 190189-97-0 methyl (3S)-3-[(tert-butoxycarbonyl)amino]-3-phenylpropionate 
• 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 
• 718611-16-6 C₂₈H₄₀N₂O₆S₂ 
• 667402-23-5 (S)-[3-(4-{ethyl-[2-(4-methanesulfonylphenyl)-acetyl]-amino}-piperidin-1-yl)-1-phenyl-propyl]-carbamic acid 1',1',1'-trichloroethoxy ester hydrochloride 
• 667402-02-0 (S)-1-benzenesulfonyl-piperidine-4-carboxylic acid [3-(4-{ethyl-[2-(4-methanesulfonyl-phenyl)-acetyl]-amino}-piperidin-1-yl)-1-phenyl-propyl]-amide 
• 667402-10-0 (S)-1-isobutyryl-piperidine-4-carboxylic acid [3-(4-{ethyl-[2-(4-methanesulfonyl-phenyl)-acetyl]-amino}-piperidin-1-yl)-1-phenyl-propyl]-amide 

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.

Chemical kinetic resolution of unprotected β-substituted β-amino acids using recyclable chiral ligands

The first chemical method for resolution of N,C-unprotected β-amino acids was developed through enantioselective formation and disassembly of nickel(II) complexes under operationally convenient conditions. The specially designed chiral ligands are inexpensive and can be quantitatively recycled along with isolation of the target β-substituted-β-amino acids in good yields and excellent enantioselectivity. The method features a broad synthetic generality including β-aryl, β-heteroaryl, and β-alkyl-derived β-amino acids. The procedure is easily scaled up, and was used for the synthetically and economically advanced preparation of the anti-diabetic drug sitagliptin. The nick of time: A chemical method for resolution of unprotected β-amino acids rac-1 was developed through enantioselective formation and disassembly of nickel(II) complexes to deliver the target β-substituted β-amino acids in good yields and excellent enantioselectivity. The chiral ligands are inexpensive and can be quantitatively recycled. The procedure was used for the preparation of anti-diabetic drug sitagliptin.

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