406681-37-6

Basic information

• Product Name: N-BOC-(S)-CYCLOPROPYLALANINE BENZYL ESTER
• Synonyms: N-BOC-(S)-CYCLOPROPYLALANINE BENZYL ESTER;(S)-benzyl 2-((tert-butoxycarbonyl)(cyclopropyl)amino)propanoate
• CAS NO: 406681-37-6
• Molecular Formula: C₁₈H₂₅NO₄
• Molecular Weight: 319.4
• Mol File: 406681-37-6.mol
• Article Data: 6

Chemical Properties

• Melting Point: 52-54°C
• Boiling Point: 428.9 °C at 760 mmHg
• Flash Point: 213.2 °C
• Appearance: /
• Vapor Pressure: 1.46E-07mmHg at 25°C
• CAS DataBase Reference: N-BOC-(S)-CYCLOPROPYLALANINE BENZYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: N-BOC-(S)-CYCLOPROPYLALANINE BENZYL ESTER(406681-37-6)
• EPA Substance Registry System: N-BOC-(S)-CYCLOPROPYLALANINE BENZYL ESTER(406681-37-6)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 406681-37-6(Hazardous Substances Data)

Usage

General Description

N-BOC-(S)-cyclopropylalanine benzyl ester is a chemical compound with the molecular formula C23H27NO4. It is a derivative of cyclopropylalanine, an amino acid commonly found in natural products and pharmaceuticals. The compound is often used in organic synthesis and pharmaceutical research as a building block for the production of various molecules with potential biological activity. Its BOC (tert-butoxycarbonyl) protecting group makes it a useful synthone in the preparation of other amino acids and peptides. Additionally, the benzyl ester group enhances the compound's stability and solubility in organic solvents, making it a versatile tool in chemical synthesis. Overall, N-BOC-(S)-cyclopropylalanine benzyl ester serves as a valuable intermediate in the development of advanced pharmaceuticals and biologically active compounds.

InChI:InChI=1/C15H19NO4.C2H6/c1-19-15(18)16-13(9-11-7-8-11)14(17)20-10-12-5-3-2-4-6-12;1-2/h2-6,11,13H,7-10H2,1H3,(H,16,18);1-2H3/t13-;/m0./s1

Upstream product

• 406681-46-7 benzyl 2-tert-butoxycarbonylamino-3-cyclopropylacrylate 
• 200482-55-9 4-cyclopropylmethylene-2-phenyl-4H-oxazol-5-one 
• 24424-99-5 di-tert-butyl dicarbonate 
• 495-69-2 Hippuric Acid 
• 629656-95-7 (2S)-2-tert-butoxycarbonylamino-4-cyclopropanecarbonylperoxy-4-oxo-butyric acid benzyl ester 
• 849340-24-5 2-tert-butoxycarbonylamino-3-cyclopropylacrylic acid benzyl ester 

Downstream Products

• 102735-53-5 (2S)-2-amino-3-cyclopropylpropanoic acid 
• 113741-17-6 (S)-2-amino-3-cyclopropylpropionic acid benzyl ester 

Relevant articles and documents

Preparation of aminophosphines

Disclosed is a process for the preparation of phosphine-aminophosphines that are useful in the formation of catalysts useful in carrying out a wide variety of reactions such as asymmetric hydrogenations, asymmetric reductions, asymmetric hydroborations, asymmetric olefin isomerizations, asymmetric hydrosilations, asymmetric allylations, asymmetric conjugate additions, and asymmetric organometallic additions. The process comprises the steps of (1) contacting a compound of formula 2 [in-line-formulae]R2P—L—NHR3??2[/in-line-formulae] with phosphorus trihalide PX3 in the presence of an inert, organic solvent and an acid acceptor to produce intermediate compound having formula 3 (2) contacting intermediate compound 3 with a reactant having the formula R1—M1, R2—M1 or a mixture thereof.

Synthesis and application of phosphinoferrocenylaminophosphine ligands for asymmetric catalysis

(Chemical Equation Presented) A new class of bidentate ligands utilizing a phosphine-aminophosphine structure has been prepared on a ferrocenylethyl backbone in a straightforward and scalable fashion from acetylferrocene. The unique property of the α-ferrocenyl carbonium ion that allows the replacement of a variety of "leaving groups" with retention of configuration greatly facilitates the synthesis, and a number of ligands have been prepared by varying the nitrogen and phosphorus substituents on the aminophosphine. These readily prepared phosphinoferrocenylaminophosphines, known as BoPhoz ligands, show surprising hydrolytic and air stability, with no degradation after 3 years open to the air. The rhodium complexes of these ligands show exceedingly high enantioselectivities (generally > 95% ee) and activities often in excess of 50 000 catalyst turnovers per hour for the asymmetric hydrogenation of a wide variety of dehydro-α-amino acid and itaconic acid derivatives. They also show high activity and good to excellent enantioselectivity for the hydrogenation of a number of α-ketoesters.

Synthesis of β-Cyclopropylalanines by Photolysis of Diacyl Peroxides

(Matrix presented) Photolysis at 254 nm of neat (no solvent) unsymmetrical diacyl peroxides derived from cyclopropane carboxylic acids and L-aspartic acid generates protected β-cyclopropylalanines in reasonable yields. Orthogonally protected 3-(trans-2-am