75857-93-1

Upstream product

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

Downstream Products

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

Relevant academic research and scientific papers

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.

Synthesis of enkephalinase inhibitor

The invention discloses a novel synthesis method of enkephalinase inhibitor Sacubitril. According to the novel synthesis method, L-Pyroglutamic acid is taken as a raw material, a plurality of steps ofreaction are carried out, and a compound I with the chirality identical to that of Sacubitril is obtained via epimerization crystallization; the compound I is subjected to acylation, and is reacted with biphenyl so as to obtain a compound II; and hydrolysis ring-opening is carried out so as to obtain a compound III; the compound III is reacted with succinic anhydride, and reduction reaction is carried out so as to obtain Sacubitril. According to the synthesis method, a novel chirality control strategy is adopted, a novel chiral center is constructed using a simple and reliable method; controlof the chiral key intermediate is carried out at the early part of the synthesis routine, so that it is beneficial for reduction of risk and cost.

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.

Oxidation of L-Proline Methyl Ester Derivatives with the Iodosylbenzene/Trimethylsilylazide Reagent Combination

Oxidation of a series of L-Proline derivatives with the (PhIO)n/TMSN3 reagent combination is reported.Subsequent utilization of the 5-azido N-acyl functionality as a N-acyl iminium ion precursor is described.

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.

Amino Acids. 7. A Novel Synthetic Route to L-Proline

Reaction of L-5-oxoproline esters L-2 with phosgene at 0 deg C gives L-5,5-dichloro-1-(chlorocarbonyl)proline esters L-6, which readily lose hydrogen chloride to form L-5-chloro-1-(chlorocarbonyl)-4,5-dehydroproline esters L-7.Catalytic hydrogenation (Pd/C, 180 bar) of L-7 yields L-1-(chlorocarbonyl)proline esters L-15 and thence, upon hydrolysis, L-proline (L-17).A 'one-pot reaction' for the whole sequence is described, starting from easily accessible L-5-oxoproline esters and yielding L-proline in 78percent overall yield and 99.7percent optical purity.

Chemical Conversion of Cyclic α-Amino Acids to α-Aminodicarboxylic Acids by Improved Ruthenium Tetroxide Oxidation

The ruthenium tetroxide (RuO4) oxidation of N-acylated L-proline esters, prepared from L-proline, was carried out under two-phase conditions to afford good yields of the corresponding lactams with no appreciable racemization, and the products were hydrolyzed in aqueous hydrochloric acid to L-glutamic acid.Similar transformation starting with racemic 2-piperidinecaboxylic acid and 2-azetidinecarboxylic acid gave 2-aminoadipic acid and aspartic acid, respectively.A novel chemical converion of cyclic α-amino acids into α-aminodicarboxylic acids has been accomplished.A new solvent system, ethyl acetate-water, was developed for this two-phase oxidation.It was found to be very useful in reducing the necessary reaction time.Keywords --- oxidation; regioselectivity; lactam synthesis; ruthenium tetroxide; cyclic α-amino acid; α-aminodicarboxylic acid; L-proline; L-glutamic acid; two-phase method; ethyl acetate-water system

THE FIRST CHEMICAL CONVERSION OF L-PROLINE TO L-GLUTAMIC ACID

The ruthenium tetroxide oxidation of N-acyl-L-proline esters gave the corresponding L-pyroglutamic acid derivatives in good yields with no appreciable racemization, which lead to the first chemical conversion of L-proline to L-glutamic acid.