386707-48-8

Basic information

• Product Name: 3-Isoxazolecarboxylic acid, 5-(2-hydroxy-2-phenylethyl)-4-(2,5,5-trimethyl-1,3-dioxan-2-yl)-, ethyl ester
• CAS NO: 386707-48-8
• Molecular Formula: C21H27NO6
• Molecular Weight: 389.448
• Mol File: 386707-48-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3-Isoxazolecarboxylic acid, 5-(2-hydroxy-2-phenylethyl)-4-(2,5,5-trimethyl-1,3-dioxan-2-yl)-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Isoxazolecarboxylic acid, 5-(2-hydroxy-2-phenylethyl)-4-(2,5,5-trimethyl-1,3-dioxan-2-yl)-, ethyl ester(386707-48-8)
• EPA Substance Registry System: 3-Isoxazolecarboxylic acid, 5-(2-hydroxy-2-phenylethyl)-4-(2,5,5-trimethyl-1,3-dioxan-2-yl)-, ethyl ester(386707-48-8)

Safety Data

• Hazardous Substances Data: 386707-48-8(Hazardous Substances Data)

Upstream product

• 15911-11-2 ethyl 4-acetyl-5-methyl-1,2-oxazole-3-carboxylate 
• 100-52-7 benzaldehyde 
• 216962-12-8 3-isoxazolecarboxylic acid 5-methyl-4-(2,5,5-trimethyl-1,3-dioxan-2-yl)-ethyl ester 

Downstream Products

• 1027381-62-9 4-((S)-2-Allylamino-2-cyano-ethyl)-5-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-2-phenyl-ethyl]-isoxazole-3-carboxylic acid ethyl ester 
• 691407-00-8 (S)-5-(2-phenyl-2-(t-butyldiphenylsilyloxy)-ethyl)-4-(2,5,5-trimethyl-1,3-dioxan-2-yl)-3-isoxazolecarboxylic acid ethyl ester 
• 691407-04-2 5-(2-phenyl-2-(t-butyldiphenylsilyloxy)-ethyl)-4-methoxycarbonylmethyl-3-isoxazolecarboxylic acid ethyl ester 
• 691407-15-5 5-(2-phenyl-2-(t-butyldiphenylsilyloxy)-ethyl)-4-(2-hydroxy-ethyl)-3-isoxazolecarboxylic acid ethyl ester 
• 691407-02-0 5-(2-phenyl-2-(t-butyldiphenylsilyloxy)-ethyl)-4-(1-keto-ethyl)-3-isoxazolecarboxylic acid ethyl ester 
• 691407-06-4 5-(2-phenyl-2-(t-butyldiphenylsilyloxy)-ethyl)-4-(2-oxo-ethyl)-3-isoxazolecarboxylic acid ethyl ester 
• 691407-10-0 (S,S)-5-(2-phenyl-2-hydroxy-ethyl)-4-(N-allyl-2-amino-2-methoxycarbonyl-ethyl)-3-isoxazolecarboxylic acid ethyl ester 
• 691406-98-1 5-(2-phenyl-2-hydroxy-ethyl)-4-(2,5,5-trimethyl-1,3-dioxan-2-yl)-3-isoxazolecarboxylic acid ethyl ester 
• 691407-11-1 (S,S)-5-(2-phenyl-2-hydroxy-ethyl)-4-(2-amino-2-methoxycarbonyl-ethyl)-3-isoxazolecarboxylic acid ethyl ester 

Relevant articles and documents

An improved procedure for the lateral lithiation of ethyl 4-acetyl-5-methyl-3-isoxazolyl carboxylate

Ethyl 4-acetyl-5-methyl-3-isoxazolyl carboxylate was smoothly lithiated at the 5-methyl position, when the 4-acetyl group was protected with a 5,5-dimethyl-1,3-dioxanyl group. The lithio anion was quenched with a variety of electrophiles such as alkyl halides, aldehydes, TMSCl, and Me3SnCl in good to excellent yields. The lithiation of the unprotected compound and the 4-acetyl group protected as 1,3-dioxolanyl both failed. The effects of different bases have been investigated and the addition of LiCl significantly increased yields. Based on variable temperature NMR studies the 5,5-dimethyl-1,3-dioxanyl group appears to occupy a single chair conformation which may facilitate lateral metalation. This represents a facile entry into 5-functionalized 3-isoxazolyl carboxylic acid derivatives as prodrugs for the AMPA glutamate neurotransmitters of the central nervous system.