75857-93-1

Basic information

• Product Name: (2S)–N-acetyl-5-oxoproline methyl ester
• Synonyms: (2S)–N-acetyl-5-oxoproline methyl ester
• CAS NO: 75857-93-1
• Molecular Weight: 185.18
• Mol File: 75857-93-1.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: (2S)–N-acetyl-5-oxoproline methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)–N-acetyl-5-oxoproline methyl ester(75857-93-1)
• EPA Substance Registry System: (2S)–N-acetyl-5-oxoproline methyl ester(75857-93-1)

Safety Data

• Hazardous Substances Data: 75857-93-1(Hazardous Substances Data)

Upstream product

• 149-87-1 Pyroglutamic acid 
• 108-24-7 acetic anhydride 
• 4931-66-2 methyl 5-oxopyrrolidine-2-carboxylate 
• 67-56-1 methanol 
• 75-36-5 acetyl chloride 
• 98-79-3 L-Pyroglutamic acid 
• 2311-25-3 N-acetyl-L-proline methyl ester 
• 147-85-3 L-proline 
• 4931-66-2 methyl (S)-pyroglutamate 
• 186581-53-3 diazomethane 
• 141695-02-5 acetic S-1-acetylpyroglutamic anhydride 

Downstream Products

• 103322-12-9 methyl N-benzoylpyroglutamate 
• 138-15-8 l-glutamic acid hydrochloride 

Relevant articles and documents

Hydroboration of vinylglycine and allylglycine as a route to boron- derivatives of α-amino acids

The hydroboration of protected vinylglycine and allylglycine with dicyclohexyl- or diisopinocampheylborane occurs chimio- and regioselectively with attachment of boron to the less substituted end of the carbon-carbon double bond. Homoserine or δ-hydroxynorvaline are readily obtained by H2O2/CH3CO2Na oxidation of dicyclohexylborane derivatives and 2-amino-4- boronobutanoic acid or 2-amino-5-boronopentanoic acid by reaction of diisopinocampheylborane derivatives with excess of ethanal and deprotection.

Oxidative functionalization of aliphatic and aromatic amino acid derivatives with H2O2 catalyzed by a nonheme imine based iron complex

The oxidation of a series of N-acetyl amino acid methyl esters with H2O2 catalyzed by a very simple iminopyridine iron(ii) complex 1 easily obtainable in situ by self-assembly of 2-picolylaldehyde, 2-picolylamine, and Fe(OTf)2 was investigated. Oxidation of protected aliphatic amino acids occurs at the α-C-H bond exclusively (N-AcAlaOMe) or in competition with the side-chain functionalization (N-AcValOMe and N-AcLeuOMe). N-AcProOMe is smoothly and cleanly oxidized with high regioselectivity affording exclusively C-5 oxidation products. Remarkably, complex 1 is also able to catalyze the oxidation of the aromatic N-AcPheOMe. A marked preference for the aromatic ring hydroxylation over Cα-H and benzylic C-H oxidation was observed, leading to the clean formation of tyrosine and its phenolic isomers.

SYNTHESIS OF 2-OXA AND 2-AZA ANALOGS OF PYRROLIZIDINE-3,5-DIONES (LUKES-SORM DILACTAM)

The synthesis of 2-oxa and 2-aza analogs of pyrrolizidine-3,5-dione (Lukes-Sorm dilactam), which has amnesia reversal activity, is reported.Optically active (+)-2-oxa and (+)-2-aza analogs and racemic 2-aza analog and its 1-methoxycarbonyl derivatives were prepared from (-)-S-pyroglutamic acid and succinimide, respectively.