330580-68-2

Basic information

• Product Name: 3,4-dihydro-3-[(phenylacetyl)amino]-2-oxo-2H-1,3-benzoxazine-7-carboxylic acid
• Synonyms: 3,4-dihydro-3-[(phenylacetyl)amino]-2-oxo-2H-1,3-benzoxazine-7-carboxylic acid
• CAS NO: 330580-68-2
• Molecular Weight: 326.309
• Mol File: 330580-68-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3,4-dihydro-3-[(phenylacetyl)amino]-2-oxo-2H-1,3-benzoxazine-7-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-dihydro-3-[(phenylacetyl)amino]-2-oxo-2H-1,3-benzoxazine-7-carboxylic acid(330580-68-2)
• EPA Substance Registry System: 3,4-dihydro-3-[(phenylacetyl)amino]-2-oxo-2H-1,3-benzoxazine-7-carboxylic acid(330580-68-2)

Safety Data

• Hazardous Substances Data: 330580-68-2(Hazardous Substances Data)

Upstream product

• 330580-66-0 3-hydroxy-4-{[2-(4-methoxybenzyl)-2-(phenylacetyl)hydrazino]methyl}benzoic acid 
• 330580-65-9 3-hydroxy-4-{[2-(4-methoxybenzyl)-2-(phenylacetyl)hydrazono]methyl}benzoic acid 
• 330580-64-8 1-(4-methoxybenzyl)-1-phenylacetylhydrazine 
• 1027199-44-5 C₁₆H₁₆N₂O₃ 
• 305849-49-4 N-(4-methoxybenzyl)-2-phenylacetamide 
• 103-80-0 phenylacetyl chloride 
• 619-12-5 4-formyl-3-hydroxybenzoic acid 
• 330580-67-1 3,4-dihydro-3-[4-methoxybenzyl(phenylacetyl)amino]-2-oxobenz[e][1,3]oxazine-7-carboxylic acid 

Relevant articles and documents

Synthesis, hydrolysis, and evaluation of 3-acylamino-3,4-dihydro-2-oxo-2H-1,3-benzoxazinecarboxylic acids and linear azadepsipeptides as potential substrates/inhibitors of β-lactam-recognizing enzymes

The title compounds can be considered as stabilized aza analogs of previously studied dihydrobenzopyranones and linear depsipeptides, which behave as substrates or inhibitors of β-lactamases. Treatment of substituted hydrazides 9b and 9b′ with a phosgene substitute resulted in a series of N-methylated 3-acylamino-3,4-dihydro-2-oxo-2H-1,3-benzoxazine-7-and -8-carboxylic acids 2b and 2b′. However, in the case of the corresponding free NH hydrazide 9a(m), a competitive cyclization gave instead a stable 4H-1,3,4-oxadiazol-5-one 10a. To avoid this unwanted cyclization, an N-(p-methoxy)-benzylated hydrazide 9b″ was prepared. After formation of the benzoxazinone ring with carbonyldiimidazole, the removal of this new N1-hydrazide protecting group was achieved with methanesulfonic acid in trifluoroacetic acid to give the expected 3-phenacetamido-3,4-dihydro-2-oxo-2H-1,3-benzoxazine-7-carboxylic acid 2a(m). The corresponding linear azadepsipeptides 5 were generally obtained by reaction of a hydrazide with 3-tert-butoxycarbonylphenyl chlorocarbonate. Hydrolysis of the title compounds in buffer at neutral pH was more rapid than anticipated because of the presence of mechanisms more facile than the classical BAC2. Hydrolysis of the cyclic azadepsipeptide 2a(m), for example, involved intramolecular nucleophilic participation by the amido side chain and a slowly hydrolyzing oxadiazolone intermediate (10a). These compounds, unlike their parent depsipeptides, were not substrates or inhibitors of β-lactamase or DD-peptidase. This result probably arises from a combination of the poor carbonyl electrophilicity and the close to planar geometry of the nitrogen atom of the oxazin-2-one ring. Wiley-VCH Verlag GmbH, 2001.