848488-70-0

Basic information

• Product Name: (1R,4R)-tert-Butyl 3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate
• Synonyms: (1R,4R)-tert-Butyl 3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate;N-Boc-4-hydroxy-D-pyrrolidine lactone;(1R,4R)-3-Oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylic acid 1,1-dimethylethyl ester;tert-butyl (1R,4R)-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate
• CAS NO: 848488-70-0
• Molecular Formula: C₁₀H₁₅NO₄
• Molecular Weight: 213.2304
• Mol File: 848488-70-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: 112-114°C &_& 112-114°C
• Boiling Point: 349.7°C at 760 mmHg
• Flash Point: 165.3°C
• Appearance: /
• Density: 1.246g/cm³
• Vapor Pressure: 4.63E-05mmHg at 25°C
• Refractive Index: 1.511
• Storage Temp.: 2-8°C
• PKA: -1.25±0.20(Predicted)
• CAS DataBase Reference: (1R,4R)-tert-Butyl 3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,4R)-tert-Butyl 3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate(848488-70-0)
• EPA Substance Registry System: (1R,4R)-tert-Butyl 3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate(848488-70-0)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 848488-70-0(Hazardous Substances Data)

Usage

General Description

The chemical "(1R,4R)-tert-Butyl 3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate" is a compound with a complex structure, containing a bicyclic ring system and multiple functional groups. The "(1R,4R)" prefix indicates the stereochemistry of the molecule, meaning that the substituents are arranged in a specific three-dimensional orientation. The tert-butyl group is a bulky and sterically hindered alkyl group, while the 3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate portion suggests the presence of a ketone, an ester, and a nitrogen-containing ring within the molecule. Overall, it is a highly specialized compound with potential applications in pharmaceuticals, materials science, and chemical synthesis.

InChI:InChI=1/C10H15NO4/c1-10(2,3)15-9(13)11-5-6-4-7(11)8(12)14-6/h6-7H,4-5H2,1-3H3/t6-,7-/m1/s1

Upstream product

• 149117-85-1 ethyl (R)-2-[(tert-butoxycarbonyl)amino]pent-4-enoate 
• 135722-56-4 ethyl (RS)-N-(tert-butoxycarbonyl)-2-aminopent-4-enoate 
• 1208237-83-5 (2R)-2-amino-3-(2-oxiranyl)propionic acid 
• 30724-02-8 hydroxyproline 
• 24424-99-5 di-tert-butyl dicarbonate 
• 13726-69-7 (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid 

Downstream Products

• 74844-91-0 (2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester 

Relevant articles and documents

Epoxy amino acids produced from allylglycines intramolecularly cyclised to yield four stereoisomers of 4-hydroxyproline derivatives

Derivatives of 2-amino-4-pentenoic acid (allylglycine) were efficiently resolved using Subtilisin or acylase. The side-chain unsaturated bond of the enantiomerically pure amino acid with tert-butoxycarbonyl (Boc) protection was smoothly epoxidized with m-chloroperbenzoic acid. When the Boc protection of the amino group was removed, the amino group intramolecularly attacked the side-chain epoxide, generating compounds with five-membered rings: the 4-hydroxyproline derivatives. Two diastereomeric products were formed through the cyclisation reaction, for example, (2S,4S)-4-hydroxyproline benzyl ester (cis-8) and (2S,4R)-4-hydroxyproline benzyl ester (trans-8) were formed from (2S)-amino acid with a side-chain epoxide. Compound (2S,4S)-4-hydroxyproline benzyl ester (cis-8) was transformed to a lactone (cis-hydroxyproline lactone, 10) with the removal of benzyl alcohol. The cis-conformation was essential for the intramolecular ester exchange reaction; in fact, no lactone formation was observed for the trans isomer (trans-8). The separation of cis-hydroxyproline lactone and the trans-isomeric hydroxyproline benzyl ester was facile and clear, in contrast to the difficult separation of cis- and trans-hydroxyproline derivatives. Thus, two diastereomers of hydroxyproline derivatives for l-hydroxyproline and also for d-hydroxyproline were obtained, i.e., four diastereomers of hydroxyproline derivatives.

QUINAZOLINE DERIVATIVES

The invention concerns quinazoline derivatives of Formula (I) wherein each of R1, R3, R20, X1, X2, Z, W, (a) and (q) have any of the meanings defined in the description; processes for their preparation, pharmaceutical compositions containing them and their use in the manufacture of a medicament for use as an antiproliferative agent in the prevention or treatment of turnours which are sensitive to inhibition of erbB receptor tyrosine kinases, particularly EGFR tyrosine kinase.