Boc-L-pyroglutamic acid methyl ester

Base Information

• Chemical Name: Boc-L-pyroglutamic acid methyl ester
• CAS No.: 108963-96-8
• Molecular Formula: C11H17NO5
• Molecular Weight: 243.26
• Hs Code.: 29337900
• European Community (EC) Number: 600-890-6
• DSSTox Substance ID: DTXSID10446511
• Nikkaji Number: J978.683J
• Wikidata: Q72450614
• Mol file: 108963-96-8.mol

Synonyms:108963-96-8;Boc-L-pyroglutamic acid methyl ester;Boc-Pyr-OMe;Methyl L-N-Boc-Pyroglutamate;(S)-1-tert-butyl 2-methyl 5-oxopyrrolidine-1,2-dicarboxylate;1-TERT-BUTYL 2-METHYL (2S)-5-OXOPYRROLIDINE-1,2-DICARBOXYLATE;1-O-tert-butyl 2-O-methyl (2S)-5-oxopyrrolidine-1,2-dicarboxylate;(S)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester;MFCD06809720;Boc-Pyr-OMe, 97%;Methyl (2S)-1-(tert-butoxycarbonyl)pyroglutamate;Methyl N-Boc-L-pyroglutamate;N-Boc-L-pyroglutamic Acid M;SCHEMBL540990;AMY3778;DTXSID10446511;FNTAOUUEQHKLIU-ZETCQYMHSA-N;1-(tert-butyl) 2-methyl (S)-5-oxopyrrolidine-1,2-dicarboxylate;AKOS005145518;AC-5690;CS-W003361;DS-1049;M2803;methyl (S)-N-tert-butoxycarbonylpyroglutamate;EN300-209244;Methyl N-(tert-Butoxycarbonyl)-L-pyroglutamate;Methyl (S)-Boc-5-pyrrolidone-2-carboxylate, 97%;Q-101863;1-(tert-Butoxycarbonyl)-5-oxo-L-proline methyl ester;N-(tert-Butoxycarbonyl)-L-pyroglutamic Acid Methyl Ester;tert-butyl (S)-2-carbomethoxy-5-oxo-pyrrolidine-1-carboxylate;1-tert-Butyl 2-methyl (2S)-5-oxopyrrolidine-1, 2-dicarboxylate;Methyl (S)-1-(tert-Butoxycarbonyl)-5-oxopyrrolidine-2-carboxylate;1-(1,1-Dimethylethyl) 2-methyl (2S)-5-oxo-1,2-pyrrolidine-dicarboxylate;1-(1,1-dimethylethyl) 2-methyl (2S)-5-oxo-1,2-pyrrolidinedicarboxylate;(2S)-5-Oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester;(S)-1-(tert-Butoxycarbonyl)-5-oxopyrrolidine-2-carboxylic Acid Methyl Ester;Methyl Boc-L-Pyroglutamate;(S)-5-oxopyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Chemical Property of Boc-L-pyroglutamic acid methyl ester

Chemical Property:

• Vapor Pressure: 2.04E-05mmHg at 25°C
• Melting Point: 69-71 °C
• Refractive Index: 1.487
• Boiling Point: 361.6 °C at 760 mmHg
• PKA: -4.28±0.40(Predicted)
• Flash Point: 172.5 °C
• PSA: 72.91000
• Density: 1.209 g/cm³
• LogP: 1.02340
• Storage Temp.: 2-8°C
• Solubility.: Soluble in dichloromethane.
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 243.11067264
• Heavy Atom Count: 17
• Complexity: 344

Purity/Quality:

99% ^*data from raw suppliers

Boc-L-Pyroglutamic acid methyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N
• Hazard Codes: Xn,N
• Statements: 36-43-50
• Safety Statements: 26-36/37-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1C(CCC1=O)C(=O)OC
• Isomeric SMILES: CC(C)(C)OC(=O)N1[C@@H](CCC1=O)C(=O)OC
• Uses: Methyl (S)-1-Boc-5-oxopyrrolidine-2-carboxylate in medicine, pharmacy, cosmetics, and industrial, artificial flavoring and fragrance agents

Technology Process of Boc-L-pyroglutamic acid methyl ester

There total 21 articles about Boc-L-pyroglutamic acid methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

di-tert-butyl dicarbonate (24424-99-5) + methyl (S)-pyroglutamate (4931-66-2) → (S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one (108963-96-8)

Guidance literature:

With dmap; In triethylamine; acetonitrile; for 3h; Ambient temperature;

DOI:10.1016/S0040-4020(01)80643-8

Reference yield: 98.0%

(S)-N-(tert-butoxycarbonyl)proline methyl ester (59936-29-7) → (S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one (108963-96-8)

Guidance literature:

With ruthenium(IV) oxide; sodium periodate; In ethyl acetate; for 6h; Ambient temperature;

Reference yield: 94.9%

methanol (67-56-1) + di-tert-butyl dicarbonate (24424-99-5) + Pyroglutamic acid (149-87-1) → (S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one (108963-96-8)

Guidance literature:

methanol; Pyroglutamic acid; With thionyl chloride; at 5 - 10 ℃; for 7h; Large scale;

di-tert-butyl dicarbonate; With dmap; In dichloromethane; for 12h; Temperature; Large scale;

upstream raw materials:

(S)-N-(tert-butoxycarbonyl)proline methyl ester

di-tert-butyl dicarbonate

methyl (S)-pyroglutamate

methyl (2S)-5-diazo-4-oxo-2-(2,2,2-trifluoroacetamido)-pentanoate

Downstream raw materials:

4-(4-methoxy-benzoyl)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

4-(4-chloro-benzoyl)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

(S)-4-Benzoyl-5-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

(2S)-4-[hydroxy(1-mesitylsulfonyl-1H-indol-3-yl)methyl]-5-oxopyrrolidine-1,2-dicarboxylic acid

Refernces

• 1、 Aillard, Boris,Kilburn, Jeremy D.,Blaydes, Jeremy P.,Tizzard, Graham J.,Findlow, Stuart,Werner, J?rn M.,Bloodworth, Sally. "Synthesis and evaluation of a (3R,6S,9S)-2-oxo-1-azabicyclo[4.3.0]nonane scaffold as a mimic of Xaa-trans-Pro in poly-l-proline type II helix conformation". . p. 4562 - 4569. Retrieved 2015.
• 2、 Stockman, Robert A.,McDermott, Paul J.,Newton, Annabella F.,Magnus, Philip. "A versatile chiral pyrrolidine aldehyde building-block for synthesis and formal synthesis of ent-nakadomarin A". . p. 559 - 562. Retrieved 2010.
• 3、 Aggarwal, Varinder K.,Astle, Christopher J.,Iding, Hans,Wirz, Beat,Rogers-Evans, Mark. "Separation of pyrrolidine allylation products by diastereoselective enzymatic ester hydrolysis". . p. 945 - 947. Retrieved 2005.
• 4、 Ticconi, Barbara,Mazzonna, Marco,Lanzalunga, Osvaldo,Lapi, Andrea. "Oxidation of α-amino acids promoted by the phthalimide N-oxyl radical: A kinetic and product study". . p. 3579 - 3585. Retrieved 2019.
• 5、 Dieterich,Young. "Synthesis of (2S,3S)-[3-2H1]- and (2S,3R)-[2,3-2H2]-proline". . p. 5455 - 5458. Retrieved 1993.
• 6、 Alnemy, Sydney,Bradley, Michael J.,Chuaqui, Claudio,Ciblat, Stephane,Hamman, Kristin B.,Hu, Shanhu,Kabro, Anzhelika,Ke, Nan,Malojcic, Goran,Marineau, Jason J.,Mihalich, Janessa,Roy, Stephanie,Savinainen, Anneli,Schmidt, Darby,Waters, Nigel J.,Whitmore, Kenneth Matthew,Wilsily, Ashraf,Winter, Dana K.,Zahler, Robert. "Discovery of SY-5609: A Selective, Noncovalent Inhibitor of CDK7". . . Retrieved 2021/11/18.
• 7、 -. "INHIBITORS OF CYCLIN-DEPENDENT KINASE 7 (CDK7)". Paragraph 124. . Retrieved 2020/05/28.