161024-80-2

Basic information

• Product Name: (R)-N-Boc-3-Amino-3-phenylpropanoic acid
• Synonyms: BOC-PHG-(C*CH2)OH;BOC PROTECTED (R)-B-PHENYLALANINE;BOC-(R)-3-AMINO-3-PHENYLPROPANOIC ACID;BOC-(R)-3-AMINO-3-PHENYLPROPIONIC ACID;BOC-BETA-PHE-OH;BOC-L-B-PHENYLALANINE;BOC-L-BETA-PHENYLALANINE;(R)-N-(TERT-BUTOXYCARBONYL)-3-AMINO-3-PHENYLPROPIONIC ACID
• CAS NO: 161024-80-2
• 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: 161024-80-2.mol
• Article Data: 8

Chemical Properties

• Melting Point: 123.4 °C
• Boiling Point: 408.52°C (rough estimate)
• Flash Point: 209.8 °C
• Appearance: White/Powder
• Density: 1.1356 (rough estimate)
• Vapor Pressure: 6.42E-08mmHg at 25°C
• Refractive Index: 1.5110 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.32±0.10(Predicted)
• BRN: 5404389
• CAS DataBase Reference: (R)-N-Boc-3-Amino-3-phenylpropanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-N-Boc-3-Amino-3-phenylpropanoic acid(161024-80-2)
• EPA Substance Registry System: (R)-N-Boc-3-Amino-3-phenylpropanoic acid(161024-80-2)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 161024-80-2(Hazardous Substances Data)

Usage

Chemical Properties

white powder

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)/t11-/m1/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 3646-50-2 3-Amino-3-phenylpropionic acid 
• 100-52-7 benzaldehyde 
• 271600-36-3 N-[phenyl(toluene-4-sulfonyl)methyl]tert-butoxycarboxyamide 
• 65451-19-6 N-(phenylacetyl)-3-amino-3-phenylpropanoic acid 
• 177896-09-2 tert-butyl benzylidenecarbamate 
• 890043-61-5 (S)-2-(tert-butoxycarbonylaminophenylmethyl)malonic acid dibenzyl ester 
• 614-19-7 (R)-3-phenyl-3-aminopropionic acid 

Downstream Products

• 760214-52-6 [(R)-1-phenyl-2-(2-pyrrolidin-1-yl-ethylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester 
• 956004-90-3 1-phenyl-2-(2H-tetrazol-5-yl)-ethylamine 
• 172823-12-0 (R)-3-(N-tert-butoxycarbonylamine)-3-phenylpropanenitrile 
• 820223-92-5 methyl (3R)-3[(tert-butoxycarbonyl)amino]-3-phenylpropanoate 
• 1227811-35-9 (R)-prop-2-ynyl 3-(tert-butoxycarbonylamino)-3-phenyl-propanoate 
• 158807-47-7 (R)-3-[N-(tert-butoxycarbonyl)amino]-3-phenylpropan-1-ol 
• 1240530-35-1 (R)-tert-butyl 3-(methoxy(methyl)amino)-3-oxo-1-phenylpropylcarbamate 
• 1609959-83-2 tert-butyl (1R)-3-{(1S)-1-[(2S)-4-methyl-1-((2R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino]-1-oxo-3-phenylpropan-2-ylamino}-3-oxo-1-phenylpropylcarbamate 

Relevant articles and documents

Organocatalytic kinetic resolution of N-boc-isoxazolidine-5-ones

Easily accessible racemic N-Boc-isoxazolidine-5-ones undergo enantioselective alcoholysis promoted by double hydrogen bond donor amine organocatalysts, resulting in their effective kinetic resolution.

Asymmetric biocatalysis of S-3-amino-3-phenylpropionic acid with new isolated Methylobacterium Y1-6

β-amino acids are widely used in drug research, and S-3-amino-3-phenylpropionic acid (S-APA) is an important pharmaceutical intermediate of S-dapoxetine, which has been approved for the treatment of premature ejaculation. Chiral catalysis is an excellent method for the preparation of enantiopure compounds. In this study, we used (±)-ethyl-3-amino-3-phenylpropanoate (EAP) as the sole carbon source. Three hundred thirty one microorganisms were isolated from 30 soil samples, and 17 strains could produce S-APA. After three rounds of cultivation and identification, the strain Y1-6 exhibiting the highest enantioselective activity of S-APA was identified as Methylobacterium oryzae. The optimal medium composition contained methanol (2.5 g/L), 1,2-propanediol (7.5 g/L), soluble starch (2.5 g/L), and peptone (10 g/L); it was shaken at 220 rpm for 4-5 days at 30 C. The optimum condition for biotransformation of EAP involved cultivation at 37 C for 48 h with 120 mg of wet cells and 0.64 mg of EAP in 1 ml of transfer solution. Under this condition, substrate ee was 92.1% and yield was 48.6%. We then attempted to use Methylobacterium Y1-6 to catalyze the hydrolytic reaction with substrates containing 3-amino-3-phenyl-propanoate ester, N-substituted-β-ethyl-3-amino-3-phenyl-propanoate, and γ-lactam. It was found that 5 compounds with ester bonds could be stereoselectively hydrolyzed to S-acid, and 2 compounds with γ-lactam bonds could be stereoselectively hydrolyzed to (-)-γ-lactam.

Novel thiazolones as HCV NS5B polymerase allosteric inhibitors: Further designs, SAR, and X-ray complex structure

Structure-activity relationships (SAR) of 1 against HCV NS5B polymerase were described. SAR explorations and further structure-based design led to the identifications of 2 and 3 as novel HCV NS5B inhibitors. X-ray structure of 3 in complex with NS5B polymerase was obtained at a resolution of 2.2 A, and confirmed the design.