60759-50-4

Upstream product

• 75-66-1 2-methylpropan-2-thiol 
• 65-85-0 benzoic acid 
• 78605-38-6 Diphenyl 2-oxo-3-oxazolinylphosphonate 
• 98-88-4 benzoyl chloride 
• 27584-70-9 4-oxazolin-2-one 

Downstream Products

• 1611-02-5 2-cyano-3-oxo-3-phenyl-propionic acid ethyl ester 
• 140-11-4 Benzyl acetate 
• 82918-45-4 3,3'-dibenzoyl-4'-methoxy-5-(trichloromethyl)<4,5'-bioxazolidinyl>-2,2'-dione 
• 93-58-3 benzoic acid methyl ester 
• 100-51-6 benzyl alcohol 
• 100-52-7 benzaldehyde 
• 82918-57-8 4-chloro-5-benzoxy-2-oxazolidinone 
• 82918-36-3 3-benzoyl-4-chloro-5-(trichloromethyl)-2-oxazolidinone 
• 82918-37-4 3,3'-dibenzoyl-4'-chloro-5-(trichloromethyl)<4,5'-bioxazolidinyl>-2,2'-dione 
• 46177-21-3 2-benzoylmalononitrile 
• 52772-11-9 S-(2-hydroxyethyl) thiobenzoate 
• 1226-99-9 2-(benzoylthio)ethyl benzoate 
• 119-61-9 benzophenone 
• 89332-65-0 cis 2-(benzamido)vinyl benzoate 

Relevant academic research and scientific papers

Chiral electrophilic 'glycinal' equivalents. New synthons for optically active α-amino acids and 4-substituted 2-oxazolidinones

The thermal reaction of 3-[(1S)-2-alkoxy-1-apocamphanecarbonyl]-2-oxazolones (21a-c) with dialkyl azodicarboxylates (9) results in exclusive formation of [4 + 2] type cycloadducts (22 and 23) with moderate levels of diastereofacial selection (up to 72% d.e.). The diastereomers thus obtained were readily purified and subsequent treatment with acidic methanol followed by removal of the auxiliary with LiBH4/MeOH (1:2) gave optically pure 4-methoxy-5-hydrazino-2-oxazolidinones (26 and 27), which serve as α-aminoaldehyde templates useful for the synthesis of a wide variety of optically active α-amino acids as well as 4-alkyl and 4-aryl-2-oxazolidinones.

ACTIVATION OF CARBOXYL GROUPS BY DIPHENYL 2-OXO-3-OXAZOLINYLPHOSPHONATE. FACILE PREPARATION OF VERSATILE REAGENTS, 3-ACYL-2-OXAZOLONES

Synthetic utility of the 2-oxazolone moiety as an excellent new leaving group is described.Based on such a function of the heterocycles, diphenyl 2-oxo-3-oxazolinylphosphonate has been newly introduced as a carboxyl-activating reagent which permits a facile direct preparation of 3-acyl-2-oxazolones and amides including peptides from a wide variety of carboxylic acids.The 3-acyl-2-oxazolides also serve as versatile reactive agents for highly chemoselective acyl-transfer to the nucleophilic species such as amines, alcohols and thiols, providing convenient and high-yield routes to amides, esters and thiol esters under mild conditions.They are also useful intermediates for ketones and alcohols.

A NEW REAGENT FOR ACTIVATING CARBOXYL GROUPS: DIPHENYL 2-OXO-3-OXAZOLINYLPHOSPHONATE

Diphenyl 2-oxo-3-oxazolinylphosphonate serves as a carboxyl-activating reagent to permit a direct preparation of versatile intermediate, 3-acyl-2-oxazolones or a one-step formation of amides from carboxylic acids.

EFFICIENT CONVERSION OF CARBOXYLIC ACIDS INTO THIOL ESTERS

A facile and direct preparation of thiol esters from carboxylic acids and thiols using diphenyl 2-oxo-3-oxazolinylphosphonate in the presence of triethylamine is described.