83846-88-2

Usage

Uses

Used in Pharmaceutical Synthesis:
(S)-phenyl[[(2,2,2-trichloroethoxy)carbonyl]amino]acetic acid is used as an intermediate in the pharmaceutical industry for the synthesis of various drugs. Its unique structure allows it to be a key component in the development of new medications, contributing to the advancement of pharmaceutical research and drug discovery.
Used in Agrochemical Production:
In the agrochemical industry, (S)-phenyl[[(2,2,2-trichloroethoxy)carbonyl]amino]acetic acid is employed as an intermediate in the production of various agrochemicals. Its role in this sector is vital for the development of new products that can enhance agricultural productivity and protect crops from pests and diseases.
Used in Organic Synthesis:
(S)-phenyl[[(2,2,2-trichloroethoxy)carbonyl]amino]acetic acid is also used as a building block in organic synthesis, allowing chemists to create a wide range of chemical compounds with diverse applications. Its versatility in this field makes it an important tool for researchers and scientists working on the development of new materials and products.
Safety Precautions:
It is important to handle (S)-phenyl[[(2,2,2-trichloroethoxy)carbonyl]amino]acetic acid with care, as it can be harmful if ingested or inhaled. Additionally, it can cause irritation to the skin and eyes. Proper safety measures, such as wearing protective gear and following established handling protocols, should be taken to minimize the risk of exposure and ensure the safety of those working with (S)-phenyl[[(2,2,2-trichloroethoxy)carbonyl]amino]acetic acid.

InChI:InChI=1/C11H10Cl3NO4/c12-11(13,14)6-19-10(18)15-8(9(16)17)7-4-2-1-3-5-7/h1-5,8H,6H2,(H,15,18)(H,16,17)/t8-/m0/s1

Upstream product

• 2935-35-5 (S)-2-phenylglycine 
• 17341-93-4 2,2,2-Trichloroethyl chloroformate 

Downstream Products

• 793718-13-5 (2S,3R)-3-((S)-2-Amino-2-phenyl-acetoxy)-2-tert-butoxycarbonylamino-butyric acid allyl ester 

Relevant academic research and scientific papers

Stereocontrolled 1,3-nitrogen migration to access chiral α-amino acids

α-Amino acids are essential for life as building blocks of proteins and components of diverse natural molecules. In both industry and academia, the incorporation of unnatural amino acids is often desirable for modulating chemical, physical and pharmaceutical properties. Here we report a protocol for the economical and practical synthesis of optically active α-amino acids based on an unprecedented stereocontrolled 1,3-nitrogen shift. Our method employs abundant and easily accessible carboxylic acids as starting materials, which are first connected to a nitrogenation reagent, followed by a highly regio- and enantioselective ruthenium- or iron-catalysed C(sp3)–H amination. This straightforward method displays a very broad scope, providing rapid access to optically active α-amino acids with aryl, allyl, propargyl and alkyl side chains, and also permits stereocontrolled late-stage amination of carboxylic-acid-containing drugs and natural products. [Figure not available: see fulltext.]

Protection of functional groups during reaction and their subsequent restoration

In the process for preparing an organic compound of the formula in which X is an amino group, a hydroxyl group or a carboxyl group, and A' is the remainder of the molecule, from an organic compound of the formula in which A is the remainder of the molecule which can undergo reaction to form A', by converting A -- X into a compound of the formula in which Z is --NH--, --O-- or a direct C--C bond, and R is a radical of the formula STR1 IN WHICH Y is a direct C--C single bond, the --CH=CH-- group or an arylene group, R1 to R4 each independently is hydrogen, halogen or an alkyl, aryl, aralkyl, alkoxycarbonyl, alkylaminocarbonyl, arylaminocarbonyl or cycloalkylaminocarbonyl radical, or R1 + r2 and R3 + R4 each independently completes a 5- or 6-membered carbocyclic ring, or R1 and R3 conjointly with the grouping --C--Y--C-- forms a carbocyclic ring with 5 or 6 carbon atoms, and Hal is halogen, Thereby to protect X, then converting A -- Z -- COOR into a compound of the formula and then treating the compound A' -- Z -- COOR to restore the group X, the improvement which comprises effecting the treatment of the compound A' -- Z -- COOR with an alkali metal compound of a complex of monovalent cobalt. The process is applicable particularly to aminocarboxylic acids including intermediates from various stages of the synthesis of penicillins and cephalosporins.