325465-01-8

Basic information

• Product Name: (S)-(4-amino-phenyl)-(tert-butyl-dimethyl-silanyloxy)-acetic acid ethyl ester
• Synonyms: (S)-(4-amino-phenyl)-(tert-butyl-dimethyl-silanyloxy)-acetic acid ethyl ester
• CAS NO: 325465-01-8
• Molecular Weight: 309.481
• Mol File: 325465-01-8.mol

Chemical Properties

• CAS DataBase Reference: (S)-(4-amino-phenyl)-(tert-butyl-dimethyl-silanyloxy)-acetic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(4-amino-phenyl)-(tert-butyl-dimethyl-silanyloxy)-acetic acid ethyl ester(325465-01-8)
• EPA Substance Registry System: (S)-(4-amino-phenyl)-(tert-butyl-dimethyl-silanyloxy)-acetic acid ethyl ester(325465-01-8)

Safety Data

• Hazardous Substances Data: 325465-01-8(Hazardous Substances Data)

Upstream product

• 851705-15-2 C₁₆H₂₅NO₅Si 
• 325464-99-1 (S)-(4-dimethylamino-phenyl)-(tert-butyl-dimethyl-silanyloxy)-acetic acid ethyl ester 
• 325464-82-2 (S)-2-[4-(dimethylamino)phenyl]-2-hydroxyacetic acid ethyl ester 
• 69739-34-0 t-butyldimethylsiyl triflate 

Downstream Products

• 13704-09-1 (S)-(-)-ethyl mandelate 
• 135348-18-4 (S)-(tert-butyl-dimethyl-silanyloxy)-phenyl-acetic acid ethyl ester 
• 10606-72-1 (R)-mandelic acid ethyl ester 

Relevant articles and documents

BIPIPERIDINYL DERIVATIVES USEFUL AS INHIBITORS OF CHEMOKINE RECEPTORS

In its many embodiments, the present invention provides a novel class of bipiperidinyl compounds as inhibitors of the CCR5 receptors, methods of preparing such compounds, pharmaceutical compositions containing one or more such compounds, methods of preparing pharmaceutical formulations comprising one or more such compounds, and methods of treatment, prevention, inhibition, or amelioration of one or more diseases associated with CCR5 using such compounds or pharmaceutical compositions. The invention also relates to the use of a combination of a compound of this invention and one or more antiviral or other agents useful in the treatment of Human Immunodeficiency Virus (HIV). The invention further relates to the use of a compound of this invention, alone or in combination with another agent, in the treatment of solid organ transplant rejection, graft v. host disease, arthritis, rheumatoid arthritis, inflammatory bowel disease, atopic dermatitis, psoriasis, asthma, allergies or multiple sclerosis.

Catalytic enantioselective Friedel-Crafts reactions of aromatic compounds with glyoxylate: A simple procedure for the synthesis of optically active aromatic mandelic acid esters

The first catalytic highly enantioselective Friedel-Crafts reaction of aromatic compounds with glyoxylate catalyzed by chiral Lewis acids is presented. The reaction has been developed for mainly aromatic amines reacting with ethyl glyoxylate in the presence of chiral bisoxazoline-copper(II) complexes as the catalyst. A series of chiral bisoxazoline-copper(II) complexes have been tested as catalysts for the reaction with N,N-dimethylaniline and it has been found that a highly regio- and enantioselective Friedel-Crafts reaction takes place in the presence of especially tert-butyl bisoxazoline-copper(II). This reaction proceeds with the formation of exclusively the para-substituted isomer in up to 95% yield and 94% ee. The reaction has been investigated for N,N-dimethylaniline under different reaction conditions and has been developed to be a catalytic highly enantioselective reaction for meta-substituted N,N-dimethylanilines, containing either electron-withdrawing or electron-donating substituents. The catalytic enantioselective Friedel-Crafts reaction also proceeds well for cyclic aromatic amines such as N-methylindoline, N-methyltetrahydroquinoline, and julolidine, where up to 91% yield and 93% ee are obtained. For polyaromatic amines high yields, but moderate ee values, of the Friedel-Crafts products are obtained. To enhance the potential of the reaction the N,N-dimethyl- and N-methyl substituents can be removed successfully leading to either the mono-N-methyl product or the free amine. The latter class of products allow for the introduction of a variety of other substituents on the aromatic nucleus. The catalytic enantioselective reaction also proceeds for heteroaromatic compounds such as 2-substituted furans which react with glyoxylate as well as trifluoropyruvates, giving up to 89% ee of the Friedel-Crafts products. Furthermore, ethyl trifluoropyruvate reacts in a highly enantioselective reaction with m-methoxyanisole to give the corresponding Friedel-Crafts product in good yield. On the basis of the experimental results and the absolute configuration of the products, the mechanism for this catalytic highly enantioselective Friedel-Crafts reaction is presented.