497872-29-4

Basic information

• Product Name: 4-Oxazolidinone, 3-ethyl-5-hydroxy-2,5-dimethyl-, (2R,5S)-rel- (9CI)
• Synonyms: 4-Oxazolidinone, 3-ethyl-5-hydroxy-2,5-dimethyl-, (2R,5S)-rel- (9CI)
• CAS NO: 497872-29-4
• Molecular Formula: C7H13NO3
• Molecular Weight: 159.18302
• Product Categories: AMINETERTIARY;ALCOHOL
• Mol File: 497872-29-4.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-Oxazolidinone, 3-ethyl-5-hydroxy-2,5-dimethyl-, (2R,5S)-rel- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Oxazolidinone, 3-ethyl-5-hydroxy-2,5-dimethyl-, (2R,5S)-rel- (9CI)(497872-29-4)
• EPA Substance Registry System: 4-Oxazolidinone, 3-ethyl-5-hydroxy-2,5-dimethyl-, (2R,5S)-rel- (9CI)(497872-29-4)

Safety Data

• Hazardous Substances Data: 497872-29-4(Hazardous Substances Data)

Upstream product

• 497872-21-6 acetic acid 3-(diethylamino)-2,3-dioxopropyl ester 
• 497872-20-5 phenylacetic acid 3-(diethylamino)-2,3-dioxopropyl ester 
• 855526-49-7 phenylacetic acid 3-(diethylamino)-2-hydroxy-3-oxopropyl ester 
• 855526-48-6 benzoic acid 3-(diethylamino)-2-hydroxy-3-oxopropyl ester 
• 855526-47-5 acetic acid 3-(diethylamino)-2-hydroxy-3-oxopropyl ester 
• 477211-58-8 N,N-diethyl-2,3-dihydroxypropanamide 
• 855526-45-3 N,N-diethyl-2,2-dimethyl-1,3-dioxolane-4-carboxamide 
• 5411-58-5 ethyl N,N-diethyloxamate 
• 889665-09-2 N,N-diethyl-3-(4-trifluoromethylphenoxy)-2-oxopropanamide 
• 855526-52-2 4-tert-butoxycarbonylamino-butyric acid 2-diethylcarbamoyl-2-oxo-ethyl ester 
• 855526-51-1 acetylglycine 3-(diethylamino)-2,3-dioxopropyl ester 
• 855526-63-5 phenyl-acetic acid 1-[ethyl-(2-oxo-propionyl)-amino]-ethyl ester 
• 855526-64-6 acetic acid 1-[ethyl-(2-oxo-propionyl)-amino]-ethyl ester 
• 847663-13-2 4-cyanobenzoic acid 3-(diethylamino)-2,3-dioxopropyl ester 

Relevant articles and documents

Photochemical cleavage and release of para-substituted phenols from α-keto amides

In aqueous media α-keto amides 4-YC6H4OCH 2COCON(R)CH(R′)CH3 (5a, R = Et, R′ = H; 5b, R = iPr, R′ = Me) with para-substituted phenolic substituents (Y = CN, CF3, H) undergo photocleavage and release of 4-YC 6H4OH with formation of 5-methyleneoxazolidin-4-ones 7a,b. For both 5a,b quantum yields range from 0.2 to 0.3. The proposed mechanism involves transfer of hydrogen from an N-alkyl group to the keto oxygen to produce zwitterionic intermediates 8a-c that eliminate the para-substituted phenolate leaving groups. The resultant imminium ions H2C=C(OH) CON+(R)=C(R′)CH3 9a,b cyclize intramolecularly to give 7a,b. The quantum yields for photoelimination decrease in CH3CN, CH2Cl2, or C6H6 due to competing cyclization of 5a,b to give oxazolidin-4-one products which retain the leaving group 4-YC6H4O- (Y = H, CN). A greater tendency to undergo cyclization in nonaqueous media is observed for the N,N-diethyl amides 5a than the N,N-diisopropyl amides 5b. With para electron releasing groups Y = CH3 and OCH3 quantum yields for photoelimination significantly decrease and 1,3-photorearrangment of the phenolic group is observed. The 1,3-rearrangement involves excited state ArO-C bond homolysis to give para-substituted phenoxyl radicals, which can be observed directly in laser flash photolysis experiments.

Time-resolved pH jump study of photochemical cleavage and release of carboxylic acids from α-keto amides

Time-resolved pH jump experiments, using laser flash photolysis and bromocresol green as an indicator, showed that photochemical cleavage and release of carboxylic acids from various α-keto amides derivatives in aqueous media occurs on the microsecond tim

Photochemical cleavage and release of carboxylic acids from α-keto amides

(Matrix presented) Carboxylate groups incorporated at the position α to the keto carbonyl of α-keto amides 1 were photochemically cleaved in aqueous media to give carboxylic acids in 70-90% yields with quantum yields of 0.3. The cleavage coproducts were diastereomeric hemiacetals 2. Prompt release of acetate and γ-aminobutyrate (GABA) in buffer was observed by difference FT-IR spectroscopy upon 355 nm laser flash photolysis. The time-constant for release of GABA was 30 ms.