2185-00-4

Usage

Preparation

Different sources of media describe the Preparation of 2185-00-4 differently. You can refer to the following data:
1. Into a suspension of finely ground glycine (15 g) in dry dioxane (750 mL), phosgene was introduced in a fine stream at 45–50 °C with efficient agitation. A clear solution was obtained after 5 h. This solution was filtered to remove unreacted glycine (1.7 g), and the dioxane was then removed under reduced pressure at a temperature below 40 °C with protection from moisture. The residue was treated with dry diethyl ether (100 mL), and the crystals of 2,5-oxazolidinedione were collected by filtration and dried over P2O5 in a vacuum desiccator. The crude product so obtained, 16 g (89%), was recrystallized from ethyl acetate/petroleum ether to yield 14.3 g (77.2%) of pure material, which showed no melting point because of polymerization.
2. Phosgene was passed in a fine stream into a suspension of finely ground glycine (15 g) in dry dioxane (750 mL) at 45–50 ℃ with efficient agitation. A clear solution was obtained after 5 h. This solution was filtered to remove unreacted glycine (1.7 g), and the dioxane was then removed under reduced pressure at a temperature below 40 ℃ under exclusion of moisture. The residue was treated with dry diethyl ether (100 mL), and the crystals of 2,5-oxazolidinedione were collected by filtration and dried over P2O5 in a vacuum desiccator. The crude product thus obtained, 16 g (89%), was recrystallized from ethyl acetate/petroleum ether to yield 14.3 g (77.2%) of pure material, which showed no melting point because of polymerization.

InChI:InChI=1/C3H3NO3/c5-2-1-4-3(6)7-2/h1H2,(H,4,6)

Upstream product

• 75-44-5 phosgene 
• 56-40-6 glycine 
• 1670-97-9 N-(methoxycarbonyl)glycine 
• 4530-20-5 BOC-glycine 
• 462-60-2 N-carbamoylglycine 
• 60-29-7 diethyl ether 
• 10026-13-8 phosphorus pentachloride 
• 1138-80-3 N-(Benzyloxycarbonyl)glycine 
• 15050-24-5 N-(benzyloxycarbonyl)glycyl chloride 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 67-66-3 chloroform 
• 18192-65-9 N-benzyloxycarbonyl-glycine trimethylsilanyl ester 
• 4596-51-4 N-(ethoxycarbonyl)glycine 
• 857802-77-8 malonic acid-monoazide 

Downstream Products

• 56414-96-1 2-amino-1-morpholinoethanone 
• 758-10-1 thioglycine 
• 623-33-6 glycine ethyl ester hydrochloride 
• 613-89-8 2-Aminoacetophenone 
• 80258-94-2 hydantoin-3-acetic acid 
• 2898-08-0 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one 
• 30302-21-7 1-(β-vinyloxyethyl)-5-phenyl-7-chloro-1,3-dihydro-2H-1,4-benzodiazepin-2-one hydrochloride 
• 33691-01-9 7-chloro-1-(2-methanesulfonyl-ethyl)-5-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one 
• 616-34-2 methoxycarbonylmethylamine 
• 94583-53-6 Z-Gly-NH-NH-CO-CH₂-NH₂ 
• 1133-42-2 1-methyl-1,2,3,4-tetrahydro-3H-1,4-benzodiazepin-2,5-dione 
• 49799-48-6 1H-1,5-benzodiazepine-2,4(3H,5H)-dione 
• 129288-40-0 2,5-Dioxo-oxazolidine-3-carboxylic acid 9H-fluoren-9-ylmethyl ester 
• 4746-64-9 2-aminoacetyl chloride 

Relevant academic research and scientific papers

Thioglycine and l-thiovaline: Biologically active H2S-donors

Thioglycine and l-thiovaline are stable under acidic and basic conditions but in the presence of bicarbonate they liberate the gasotransmitter H 2S. In cells both thioamino acids were proven to enhance cGMP formation and promote vasorelaxation in mouse aortic rings. Given that H 2S is known to lower arterial hypertension, reduce oxidative stress and exhibit cardioprotective effects in preclinical models, H2S donors hold promise as novel treatments for cardiovascular diseases.

METHOD OF SYNTHESIZING N-CARBOXYANHYDRIDE USING FLOW REACTOR

PROBLEM TO BE SOLVED: To provide a synthesis method that allows high-yield continuous production of a compound of interest in synthesis and production of N-carboxyanhydride (NCA) and the like using a flow reactor. SOLUTION: In a synthesis method using a flow reactor 100, a basic solution adjusted in advance to a pH of 7-14 becomes acidic with a pH of 0-7, or an acidic solution adjusted in advance to a pH of 0-7 becomes basic with a pH of 7-14, within 60 seconds after the start of mixture of at least two ingredient solutions. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2020,JPOandINPIT

METHOD FOR PRODUCING AMINO ACID-N-CARBOXYLIC ACID ANHYDRIDE

PROBLEM TO BE SOLVED: To provide: a method for safely and efficiently producing amino acid-N-carboxylic acid anhydride; and a method for producing peptide by using the obtained amino acid-N-carboxylic acid anhydride. SOLUTION: The method for producing an amino acid-N-carboxylic acid anhydride according to the present invention is characterized in that the amino acid-N-carboxylic acid anhydride is represented by the following formula (II), and a step of irradiating a composition containing a halogenated methane and an amino acid compound represented by the following formula (I) with high energy light in the presence of oxygen is included. [In the formula, R1 represents an amino acid side chain group in which the reactive group is protected, and R2 represents H or the like.]. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT

Rapid and Mild Synthesis of Amino Acid N-Carboxy Anhydrides: Basic-to-Acidic Flash Switching in a Microflow Reactor

Polymerization of N-carboxy anhydrides (NCAs) is the primary process used to prepare polypeptides. The synthesis of various pure NCAs is key to the efficient synthesis of polypeptides. The only practical method that can be used to synthesize NCAs requires harsh acidic conditions that make acid-labile substrates unusable and results in an undesired ring opening of NCAs. Basic-to-acidic flash switching and subsequent flash dilution technology in a microflow reactor was used to demonstrate the synthesis of NCAs. It is both rapid (0.1 s) and mild (20 °C) and includes substrates containing acid-labile functional groups. The basic-to-acidic flash switching enabled both an acceleration of the desired NCA formation and avoided the undesired ring opening of NCAs. The flash dilution precluded the undesired decomposition of acid-labile functional groups. The developed process allowed the synthesis of various NCAs which cannot be readily synthesized using conventional batch methods.

Multi-responsive polypeptide hydrogels derived from: N -carboxyanhydride terpolymerizations for delivery of nonsteroidal anti-inflammatory drugs

A polypeptide-based hydrogel system, when prepared from a diblock polymer with a ternary copolypeptide as one block, exhibited thermo-, mechano- and enzyme-responsive properties, which enabled the encapsulation of naproxen (Npx) during the sol-gel transition and its release in the gel state. Statistical terpolymerizations of l-alanine (Ala), glycine (Gly) and l-isoleucine (Ile) NCAs at a 1:1:1 feed ratio initiated by monomethoxy monoamino-terminated poly(ethylene glycol) afforded a series of methoxy poly(ethylene glycol)-block-poly(l-alanine-co-glycine-co-l-isoleucine) (mPEG-b-P(A-G-I)) block polymers. β-Sheets were the dominant secondary structures within the polypeptide segments, which facilitated a heat-induced sol-to-gel transition, resulting from the supramolecular assembly of β-sheets into nanofibrils. Deconstruction of the three-dimensional networks by mechanical force (sonication) triggered the reverse gel-to-sol transition. Certain enzymes could accelerate the breakdown of the hydrogel, as determined by in vitro gel weight loss profiles. The hydrogels were able to encapsulate and release Npx over 6 days, demonstrating the potential application of these polypeptide hydrogels as an injectable local delivery system for small molecule drugs.

Esterification of amino acids and mono acids using triphosgene

Alkyl esters of several amino acids and acids were prepared using triphosgene [trichloromethyl carbonate, TPA (2)].

A new simple and quantitative synthesis of α-aminoacid-N-carboxyanhydrides (oxazolidines-2,5-dione)

Nitrosation of chiral N-carbamoylaminoacids with a mixture of NO and O2 gives, with the same configuration and in quantitative yield the corresponding α-aminoacid-N-carboxyanhydrides (NCA), well known precursors of peptides. The by products of this reaction are N2 and H2O. Copyright (C) 1996 Elsevier Science Ltd.

New routes to 1,4-benzodiazepin-2,5-diones

1,4-benzodiazepin-2,5-diones have been synthesized in good overall yields by two routes, the first one by cyclisation of dipeptides prepared from Boc anthranilic acid and α-amino acid methyl esters, the second one by reaction of N-carboxy α-amino acid anhydrides with Boc anthranilic acid.

Electroactive Poly(amino acids). Part 2. Copolymers of Nε-4-Nitrobenzoyl-L-lysine with Inactive Amino Acids: Modified Electrodes with these Polymers and Poly(pyrrole) and with Poly(1-pyrrole)

Co-polymerization of the N-carboxyanhydrides derived from Nε-4-nitrobenzoyl-L-lysine (NBL) and one of the amino acids, Nε-4-benzoyl-L-lysine, L-leucine, and glycine afforded elecroactive materials.These can be adsorbed onto platinum from dimethylacetamide solution.The electrochemical response of the adsorbed layers quickly deteriorates to give broad peaks on continuous cyclic voltammetry.Determination of the response is thought to be due to a combination of poor adhesion and conformational changes which accompany charging and discharging of the film.Poly(1- pyrrole) forms a coherent film on platinum.It shows a good response due to the nitro group on continuous cyclic voltammetry.The height of this response falls with time due to loss of electroactive material.Poly(NBL) also forms a film by adsorption onto a 20-60 nm thick layer of poly(pyrrole) and the composite gives a response on continuous cyclic voltammetry that is much more stable than any of the previous cases.Coating platinum with poly(NBL) and then with poly(pyrrole) also gives a stable composite.