132622-85-6

Basic information

• Product Name: (2R,4R)-1-(tert-butoxycarbonyl)-4-cyanopyrrolidine-2-carboxylic acid
• Synonyms: (2R,4R)-1-(tert-butoxycarbonyl)-4-cyanopyrrolidine-2-carboxylic acid;(2R,4R)-4-Cyano-1,2-pyrrolidinedicarboxylic acid 1-(tert-butyl) ester;(2R,4R)-4-Cyanopyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester
• CAS NO: 132622-85-6
• Molecular Formula: C₁₁H₁₆N₂O₄
• Molecular Weight: 240.25574
• Mol File: 132622-85-6.mol

Chemical Properties

• Melting Point: 134-135℃
• Boiling Point: 423.5±45.0 °C(Predicted)
• Appearance: /
• Density: 1.25
• PKA: 3.51±0.40(Predicted)
• CAS DataBase Reference: (2R,4R)-1-(tert-butoxycarbonyl)-4-cyanopyrrolidine-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,4R)-1-(tert-butoxycarbonyl)-4-cyanopyrrolidine-2-carboxylic acid(132622-85-6)
• EPA Substance Registry System: (2R,4R)-1-(tert-butoxycarbonyl)-4-cyanopyrrolidine-2-carboxylic acid(132622-85-6)

Safety Data

• Hazardous Substances Data: 132622-85-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
(2R,4R)-1-(tert-butoxycarbonyl)-4-cyanopyrrolidine-2-carboxylic acid is used as a key intermediate in the development of various pharmaceuticals. Its unique structure and functional groups make it a versatile building block for creating complex organic compounds with potential therapeutic applications.
Used in Organic Chemistry Research:
In the field of organic chemistry, (2R,4R)-1-(tert-butoxycarbonyl)-4-cyanopyrrolidine-2-carboxylic acid is utilized for studying the synthesis and reactions of chiral compounds. Its well-defined stereochemistry at the 2nd and 4th positions allows researchers to explore the effects of stereoselectivity on chemical reactions and the properties of the resulting molecules.
Used in Drug Development:
(2R,4R)-1-(tert-butoxycarbonyl)-4-cyanopyrrolidine-2-carboxylic acid is employed as a building block in drug development, where its incorporation into new molecular entities can lead to the discovery of innovative medications with improved efficacy and selectivity. Its presence in the molecular structure can influence the pharmacokinetics and pharmacodynamics of the resulting drug candidates.

Upstream product

• 132622-83-4 (4R)-1-(tert-butoxycarbonyl)-4-cyano-D-proline ethyl ester 
• 132622-76-5 (4S)-1-(tert-butoxycarbonyl)-4-bromo-D-proline ethyl ester 
• 77450-00-1 (2R,4R)-4-hydroxyproline-1,2-dicarboxylic acid 1-tert-butyl 2-ethyl ester 

Downstream Products

• 132622-86-7 (4R)-1-(tert-butoxycarbonyl)-4-(aminomethyl)-D-proline 
• 132622-87-8 (4R)-1-(tert-butoxycarbonyl)-4-<<<<(p-toluenesulfonyl)imino>aminomethyl>amino>methyl>-D-proline 
• 136124-31-7 (2R,4S)-4-[({Methylsulfanyl-[(E)-toluene-4-sulfonylimino]-methyl}-amino)-methyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 

Relevant articles and documents

Chimeric amino acid analogues

A chimeric amino acid analogue is provided suitable for incorporating into peptides which compound is represented by Formula 1: STR1 where P1 is preferably an amine protecting agent, and P2 and P3 are preferably amine or guanidine protecting agents. X can be OH, halide, or preferably an activating group suitable for conjugating the compound of Formula 1 to a peptide by conventional means, and m and n are 0-1 and 0-2 respectively. Peptides containing the chimeric amino acid analog are provided and include a platelet-aggregation inhibitor represented by where Aaa1 is Gly or H, Cpdl is the compound of Formula 1 which has been deprotected and Aaa2 is a hydrophobic amino acid preferably Val.

Conformationally Restricted Arginine Analogues

We report the practical synthesis and structural characterization of a set of conformationally constrained protected arginine analogues.These enantiomerically pure analogues have the general structure 1 and are prepared in seven to eight steps from the co