109384-24-9

Basic information

• Product Name: (2S,4R)-1-Boc-2-carbamoyl-4-hydroxypyrrolidine
• Synonyms: (2S,4R)-1-Boc-2-carbamoyl-4-hydroxypyrrolidine;(2S,4R)-tert-butyl 2-carbamoyl-4-hydroxypyrrolidine-1-carboxylate;-tert-Butyl 2-carbamoyl-4-hydroxypyrrolidine-1-carboxylate;tert-butyl (2S,4R)-2-carbamoyl-4-hydroxypyrrolidine-1-carboxylate;1-Pyrrolidinecarboxylic acid, 2-(aminocarbonyl)-4-hydroxy-, 1,1-dimethylethyl ester, (2S,4R)-
• CAS NO: 109384-24-9
• Molecular Formula: C₁₀H₁₈N₂O₄
• Molecular Weight: 230.26092
• Mol File: 109384-24-9.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 424.77°C at 760 mmHg
• Flash Point: 210.693°C
• Appearance: /
• Density: 1.263g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.532
• Storage Temp.: 2-8°C
• PKA: 14.33±0.40(Predicted)
• CAS DataBase Reference: (2S,4R)-1-Boc-2-carbamoyl-4-hydroxypyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,4R)-1-Boc-2-carbamoyl-4-hydroxypyrrolidine(109384-24-9)
• EPA Substance Registry System: (2S,4R)-1-Boc-2-carbamoyl-4-hydroxypyrrolidine(109384-24-9)

Safety Data

• Hazardous Substances Data: 109384-24-9(Hazardous Substances Data)

Usage

General Description

"(2S,4R)-1-Boc-2-carbamoyl-4-hydroxypyrrolidine" is a chemical compound that belongs to the class of organic compounds known as N-Boc amino acids and derivatives. These are compounds containing a moiety derived from an amino acid in which the carboxy group has been replaced by a tertiary butoxycarbonyl (Boc) group. Its molecular formula is C10H18N2O4 and it contains the elements carbon, hydrogen, nitrogen, and oxygen. The chemical is commonly used in pharmaceuticals and medical research, particularly in the synthesis of various drugs. Its stable chiral configuration makes it useful in the development of pharmaceuticals that require specific stereochemistry. As such, its safety, toxicity, and potential effects are largely dependent on its use and transformation in a medicinal context.

InChI:InChI=1/C10H18N2O4/c1-10(2,3)16-9(15)12-5-6(13)4-7(12)8(11)14/h6-7,13H,4-5H2,1-3H3,(H2,11,14)/t6-,7+/m1/s1

Upstream product

• 13726-69-7 (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid 
• 1336-21-6 ammonium hydroxide 
• 541-41-3 chloroformic acid ethyl ester 
• 80029-43-2 1-hydroxybenzotriazol-hydrate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 74844-91-0 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate 

Downstream Products

• 483366-12-7 (2S,4R)-N-Boc-2-cyano-4-hydroxypyrrolidine 
• 928776-72-1 5-benzyloxy-2-(5-tert-butyldimethylsilyloxy-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione 
• 928776-73-2 5-benzyloxy-2-(5-hydroxy-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione 

Relevant articles and documents

Synthesis and structure-activity relationships of potent 3- or 4-substituted-2-cyanopyrrolidine dipeptidyl peptidase IV inhibitors

A series of 3- or 4-substituted-2-cyanopyrrolidines were synthesized and evaluated as dipeptidyl peptidase IV inhibitors. Dipeptidyl peptidase IV (DPP-IV) inhibitors have attracted attention as potential drugs for use in the treatment of type 2 diabetes because they prevent degradation of glucagon-like peptide-1 (GLP-1) and extend its duration of action. A series of 2-cyanopyrrolidines are among the most potent of DPP-IV inhibitors. We focused our attention on substitutions at the 3- or 4-position of 2-cyanopyrrolidines and synthesized and evaluated various derivatives. Among them, the 4-fluoro derivative was found to exhibit better DPP-IV inhibitory activity and higher plasma drug concentrations after oral administration to rats than the 4-unsubstituted derivative. We report here on the synthesis and biological data of the aforementioned derivatives.

(4-HYDROXYPYRROLIDIN-2-YL)-HETEROCYCLIC COMPOUNDS AND METHODS OF USE THEREOF

The present disclosure relates to bifunctional compounds of formula (I), which can be used as modulators of targeted ubiquitination. In particular, the present disclosure is directed to compounds which contain on one end a VHL ligand moiety, which binds to the VHL E3 ubiquitin ligase, and on the other end a moiety that binds a target protein such that degradation of the target protein/polypeptide is effectuated. Also disclosed are VHL ligands of formula (III).

NOVEL PROCESSES FOR THE PREPARATION OF DPP IV INHIBITORS

The present invention relates to novel processes for preparing DPP-IV inhibitors having the structure of formula I, and pharmaceutically acceptable salt thereof, which are useful for treatment of Type 2 diabetes.