85136-12-5

Basic information

• Product Name: (S)-2-PYRROLIDONE-5-CARBOXYLIC ACID T-BUTYL ESTER
• Synonyms: (S)-2-PYRROLIDONE-5-CARBOXYLIC ACID T-BUTYL ESTER;tert-butyl 5-oxo-DL-prolinate;(S)-2-Pyrrolidone-5-carboxylicacidtert-butylester;(±)-5-Oxoproline 1,1-dimethylethyl ester;5-Oxo-DL-proline 1,1-dimethylethyl ester;rac-5-Oxopyrrolidine-2α*-carboxylic acid tert-butyl ester;Einecs 285-735-7;tert-Butyl 5-oxo-2-pyrrolidinecarboxylate
• CAS NO: 85136-12-5
• Molecular Formula: C₉H₁₅NO₃
• Molecular Weight: 185.22
• EINECS: 285-735-7
• Product Categories: chiral;Chiral Reagent
• Mol File: 85136-12-5.mol
• Article Data: 54

Chemical Properties

• Melting Point: 93 °C(Solv: ethyl ether (60-29-7); ligroine (8032-32-4))
• Boiling Point: 319.2 °C at 760 mmHg
• Flash Point: 146.8 °C
• Appearance: /
• Density: 1.099 g/cm³
• PKA: 14.65±0.40(Predicted)
• CAS DataBase Reference: (S)-2-PYRROLIDONE-5-CARBOXYLIC ACID T-BUTYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-PYRROLIDONE-5-CARBOXYLIC ACID T-BUTYL ESTER(85136-12-5)
• EPA Substance Registry System: (S)-2-PYRROLIDONE-5-CARBOXYLIC ACID T-BUTYL ESTER(85136-12-5)

Safety Data

• Hazardous Substances Data: 85136-12-5(Hazardous Substances Data)

Usage

General Description

(S)-2-Pyrrolidone-5-carboxylic acid T-butyl ester, also known as L-Pyroglutamic acid T-butyl ester, is a chemical compound used in the synthesis of pharmaceuticals and agrochemicals. It is a derivative of L-Pyroglutamic acid, an amino acid commonly found in plants and animals. (S)-2-PYRROLIDONE-5-CARBOXYLIC ACID T-BUTYL ESTER is commonly used as a building block in the synthesis of various drugs, such as antipsychotics and anti-epileptics. Because of its versatile nature, it has a wide range of applications in the pharmaceutical and agricultural industries. Additionally, it is used as a precursor in the production of specialty chemicals and in the development of new materials.

Upstream product

• 540-88-5 acetic acid tert-butyl ester 
• 98-79-3 L-Pyroglutamic acid 
• 115-11-7 isobutene 
• 74936-93-9 (S)-5-oxopyrrolidine-2-carbonyl chloride 
• 75-65-0 tert-butyl alcohol 
• 529483-99-6 t-butyl (4S)-t-6-[(5'S)-5'-(tert-butyloxycarbonyl)-2'-oxo-pyrrolidin-1'-yl]-r-4,c-5-dihydroxy-1,2-oxazinane-2-carboxylate 
• 529484-01-3 benzyl (3S)-c-6-[(5'S)-5'-(tert-butyloxycarbonyl)-2'-oxo-pyrrolidin-1'-yl]-t-4,t-5-dihydroxy-r-3-methyl-1,2-oxazinane-2-carboxylate 
• 91229-91-3 tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate 
• 36016-38-3 tert-Butyl N-hydroxycarbamate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 175789-29-4 (3S,6S)-6-((S)-2-tert-Butoxycarbonyl-5-oxo-pyrrolidin-1-yl)-3-methyl-3,6-dihydro-[1,2]oxazine-2-carboxylic acid benzyl ester 
• 529483-98-5 t-butyl (6S)-6-[(5'S)-5'-t-butyloxycarbonyl-2'-oxo-pyrrolidin-1'-yl]-3,6-dihydro-2H-1,2-oxazine-2-carboxylate 
• 507-19-7 t-butyl bromide 
• 507-20-0 tertiary butyl chloride 

Downstream Products

• 91229-91-3 tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate 
• 98013-97-9 N-(N-carbobenzyloxyglycyl)-L-pyroglutamic acid tert-butyl ester 
• 97998-60-2 N-(N-carbobenzyloxy-L-alanyl)-L-pyroglutamic acid tert-butyl ester 
• 80125-26-4 tert-butyl (2S)-1-<(2S)-3-acetylthio-2-methylpropanoyl>pyroglutamate 
• 98049-19-5 -(S)-alanyl>-(S)-pyroglutamic acid tert-butyl ester 
• 98049-20-8 -(R)-alanyl>-(S)-pyroglutamic acid tert-butyl ester 
• 81470-51-1 tert-butyl N-benzyloxycarbonyl-L-pyroglutamate 
• 90741-27-8 (S)-tert-butyl 1-benzyl-5-oxopyrrolidine-2-carboxylate 
• 378238-37-0 tert-butyl N-benzenesulfonyl-(S)-pyroglutamate 
• 454253-77-1 tert-butyl N-benzoyl-(S)-pyroglutamate 
• 591225-77-3 tert-butyl N-(p-nitrobenzoyl)-(S)-pyroglutamate 
• 380223-07-4 (S)-1-(2-Azido-benzoyl)-5-oxo-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 740039-33-2 (-)-(5S)-methyl-2-imino-1-methylpyrrolidine-2-carboxylate 
• 896100-50-8 (S)-7-benzyl 1-tert-butyl 2-(tert-butoxycarbonyl)-5-oxoheptanedioate 

Relevant articles and documents

Preparation method of (S)-1 - (benzyloxycarbonyl) -5 -oxo-pyrrolidine -2 - formic acid

The invention discloses a preparation method of (S)-1 - (benzyloxycarbonyl) -5 -oxo-pyrrolidine -2 - formic acid, which mainly solves the complexity in the original process, and is long in period and high in cost. The method specifically comprises first steps of preparing L - benzyloxycarbonyl N - glutamic acid from - L - glutamic acid and a benzyloxycarbonyl donor, second steps of intramolecular condensation cyclization N - benzyloxycarbonyl - L - glutamic acid to obtain the N -benzyloxycarbonyl - L - glutamic acid crude product. The third The crude N - benzyloxycarbonyl - L - glutamic acid crude product and the organic amine base are mixed, and the organic amine salt form is prepared by the solubility of the product in a solvent, fourth (N -) - L - (benzyloxycarbonyl) S oxopyrrolidine -1 - formic acid is prepared by desalinating -5 - benzyloxycarbonyl -2 - glutamic acid. To the method, the high-purity product is prepared, and the yield and the quality are greatly improved.

L-Y-METHYLENEGLUTAMINE COMPOUNDS AND METHODS OF USE

Disclosed are substantially pure L-y-methyleneglutamine, L-y- methyleneglutamic acid, and/or amide derivatives, and methods of use thereof. In particular, the presently disclosed subject matter relates to L-y-methyleneglutamine, L-y-methyleneglutamic acid, and/or amide derivatives thereof, and methods of treating cancer. The method comprises administering one or more substantially pure L-y-methyleneglutamine, L-y-methyleneglutamic acid, and/or amide derivatives to a subject in need thereof.

Rapid and Mild Lactamization Using Highly Electrophilic Triphosgene in a Microflow Reactor

Lactams are cyclic amides that are indispensable as drugs and as drug candidates. Conventional lactamization includes acid-mediated and coupling-agent-mediated approaches that suffer from narrow substrate scope, much waste, and/or high cost. Inexpensive, less-wasteful approaches mediated by highly electrophilic reagents are attractive, but there is an imminent risk of side reactions. Herein, a methods using highly electrophilic triphosgene in a microflow reactor that accomplishes rapid (0.5–10 s), mild, inexpensive, and less-wasteful lactamization are described. Methods A and B, which use N-methylmorpholine and N-methylimidazole, respectively, were developed. Various lactams and a cyclic peptide containing acid- and/or heat-labile functional groups were synthesized in good to high yields without the need for tedious purification. Undesired reactions were successfully suppressed, and the risk of handling triphosgene was minimized by the use of microflow technology.