64923-12-2

Basic information

• Product Name: Glycine, N-(phenylmethylene)-, 1,1-dimethylethyl ester
• CAS NO: 64923-12-2
• Molecular Formula: C13H17NO2
• Molecular Weight: 219.283
• Mol File: 64923-12-2.mol
• Article Data: 20

Chemical Properties

• CAS DataBase Reference: Glycine, N-(phenylmethylene)-, 1,1-dimethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Glycine, N-(phenylmethylene)-, 1,1-dimethylethyl ester(64923-12-2)
• EPA Substance Registry System: Glycine, N-(phenylmethylene)-, 1,1-dimethylethyl ester(64923-12-2)

Safety Data

• Hazardous Substances Data: 64923-12-2(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 38024-18-9 glycine tert-butyl ester, acetic acid salt 
• 27532-96-3 glycine tert-butyl ester hydrochloride 
• 6456-74-2 Glycine tert-butyl ester 

Downstream Products

• 15911-73-6 tert-Butyl 2-aminohexanoate 

Relevant articles and documents

General Asymmetric Synthesis of Densely Functionalized Pyrrolidines via Endo-Selective [3+2] Cycloaddition of β-Quaternary-Substituted Nitroalkenes and Azomethine Ylides

A scalable endo-selective synthesis of 2,3,4,5-tetrasubstituted pyrrolidines via cycloaddition of nitroalkenes and azomethine ylides is reported using a P,N-type ferrocenyl ligand and [Cu(OTf)]2·C6H6. The robust method is tolerant of a wide range of functionalities, including rarely reported quaternary nitroalkene substitution and heteroaromatic and hindered ortho-substituted arenes on the azomethine ylide. Subsequent transformations highlight the utility of the method in the synthesis of densely functionalized small molecules suitable for fragment-based drug discovery and the cystic fibrosis C2-corrector clinical candidate ABBV-3221.

Well-Designed Phosphine-Urea Ligand for Highly Diastereo- and Enantioselective 1,3-Dipolar Cycloaddition of Methacrylonitrile: A Combined Experimental and Theoretical Study

A novel chiral phosphine-urea bifunctional ligand has been developed for Cu-catalyzed asymmetric 1,3-dipolar cycloaddition of iminoesters with methacrylonitrile, a long-standing challenging substrate in asymmetric catalysis. Distortion-interaction energy analysis based on density functional theory (DFT) calculations reveals that the distortion energy plays an important role in the observed enantioselectivity, which can be attributed to the steric effect between the phosphine ligand and the dipole reactant. DFT calculations also indicate that nucleophilic addition is the enantioselectivity-determining step and hydrogen bonding between the urea moiety and methacrylonitrile assists in control of the diastereo- and enantioselectivity. By a combination of metal catalysis and organocatalysis, excellent diastereo- and enantioselectivities (up to 99:1 diastereomeric ratio, 99% enantiomeric excess) as well as good yields are achieved. A wide range of substitution patterns of both iminoester and acrylonitrile is tolerated by this catalyst system, providing access to a series of highly substituted chiral cyanopyrrolidines with up to two quaternary stereogenic centers. The synthetic utility is demonstrated by enantioselective synthesis of antitumor agent ETP69 with a pivotal nitrile pharmacophore and an all-carbon quaternary stereogenic center.

Substituted Pyrrolidines and Methods of Use

The invention discloses compounds of Formula (I) wherein R1, R2, R2A, R3, R3A, R4, R4A, and R5 are as defined herein. The present invention relates to compounds and their use in the treatment of cystic fibrosis, methods for their production, pharmaceutical compositions comprising the same, and methods of treating cystic fibrosis by administering a compound of the invention.