(S)-di-tert-butyl 5-oxopyrrolidine-1,2-dicarboxylate

Base Information

• Chemical Name: (S)-di-tert-butyl 5-oxopyrrolidine-1,2-dicarboxylate
• CAS No.: 91229-91-3
• Molecular Formula: C14H23NO5
• Molecular Weight: 285.34
• Hs Code.: 2933790090
• DSSTox Substance ID: DTXSID60456327
• Nikkaji Number: J977.224C
• Wikidata: Q72450685
• Mol file: 91229-91-3.mol

Synonyms:91229-91-3;(S)-di-tert-butyl 5-oxopyrrolidine-1,2-dicarboxylate;(s)-n-boc-2-pyrrolidone-5-carboxylic acid tert-butyl ester;(S)-N-Boc-2-pyrrolidone-5-carboxylic acid t-butyl ester;(S)-N-Boc-pyroglutamic acid tert-butyl ester;ditert-butyl (2S)-5-oxopyrrolidine-1,2-dicarboxylate;di-tert-butyl (s)-5-oxopyrrolidine-1,2-dicarboxylate;(s)-n-alpha-t-butyloxycarbonyl-pyroglutamic acid t-butyl ester;Boc-L-pyroglutamic acid tert-butyl ester;di-tert-butyl (2s)-5-oxopyrrolidine-1,2-dicarboxylate;MFCD03094770;Boc-Py;boc-pyr(otbu)-oh;Boc-L-Pyr-Otbu;boc-(2s)-pyroglut-tbu;t-butyl N-boc-pyroglutamate;SCHEMBL713924;(S)-Di-tert-butyl5-oxopyrrolidine-1,2-dicarboxylate;DTXSID60456327;tert-Butyl N-Boc-L-pyroglutamate;INVKHBRFFCQICU-VIFPVBQESA-N;1,2-di-tert-butyl (2S)-5-oxopyrrolidine-1,2-dicarboxylate;AMY25340;2-((2-hydroxyethyl)amino)-benzoicaci;AKOS015841393;GS-3393;1,2-Pyrrolidinedicarboxylic acid, 5-oxo-, bis(1,1-dimethylethyl) ester,(2S)-;(s)-n-boc-pyroglutamic acid tertbutyl ester;N-Boc-L-pyroglutamic Acid tert-Butyl Ester;B5216;CS-0046809;tert-butyl N-tert-butoxycarbonylpyroglutamate;tert-butyl N-tert-butoxycarbonyl-pyroglutamate;(S)-tert-Butyl N-tert-butoxycarbonylpyroglutamate;10.14272/INVKHBRFFCQICU-VIFPVBQESA-N.1;doi:10.14272/INVKHBRFFCQICU-VIFPVBQESA-N.1;J-502510;tert-Butyl N-(tert-Butoxycarbonyl)-L-pyroglutamate;(S)-N-Boc-2-Pyrrolidone-5-carboxylic acidtert-butyl ester;1-(tert-Butoxycarbonyl)-5-oxo-L-proline tert-butyl ester;(S)-5-Oxopyrrolidine-1,2-dicarboxylate Di-tert-butyl Ester;N-(tert-Butoxycarbonyl)-L-pyroglutamic Acid tert-Butyl Ester;(S)-5-oxo-pyrrolidine-1,2-dicarboxylic acid di-tert-butyl ester;(s)-n-alpha-tert-butyloxycarbonyl-pyroglutamic acid t-butyl ester;(2S)-1-(tert-Butoxycarbonyl)-5-oxopyrrolidine-2-carboxylic acid tert-butyl ester

Chemical Property of (S)-di-tert-butyl 5-oxopyrrolidine-1,2-dicarboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 55.0 to 59.0 °C
• Refractive Index: 1.485
• Boiling Point: 396.9 °C at 760 mmHg
• PKA: -4.28±0.40(Predicted)
• Flash Point: 193.9 °C
• PSA: 72.91000
• Density: 1.102
• LogP: 2.19210
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 285.15762283
• Heavy Atom Count: 20
• Complexity: 416

Purity/Quality:

98%,99%, ^*data from raw suppliers

(S)-N-Boc-2-pyrrolidone-5-carboxylicacidt-butylester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)C1CCC(=O)N1C(=O)OC(C)(C)C
• Isomeric SMILES: CC(C)(C)OC(=O)[C@@H]1CCC(=O)N1C(=O)OC(C)(C)C

Technology Process of (S)-di-tert-butyl 5-oxopyrrolidine-1,2-dicarboxylate

There total 29 articles about (S)-di-tert-butyl 5-oxopyrrolidine-1,2-dicarboxylate 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) + L-t-butyl pyroglutamate (35418-16-7,85136-12-5) → tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate (91229-91-3)

Guidance literature:

With dmap; In acetonitrile; for 0.5h;

DOI:10.1016/j.tetlet.2008.01.098

Reference yield: 95.0%

N-BOC-proline tert-butyl ester (91237-84-2) → tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate (91229-91-3)

Guidance literature:

With ruthenium(IV) oxide; sodium periodate; In ethyl acetate; for 2h; Ambient temperature;

Reference yield: 89.0%

di-tert-butyl dicarbonate (24424-99-5) + L-N-t-butoxycarbonylpyroglutamic acid (53100-44-0,160347-90-0) → tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate (91229-91-3)

Guidance literature:

With dmap; triethylamine; In acetonitrile; Ambient temperature;

DOI:10.1039/p19960000507

upstream raw materials:

1-(tert-butoxycarbonyl)-L-proline

di-tert-butyl dicarbonate

L-t-butyl pyroglutamate

benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

Downstream raw materials:

L-Pyroglutamic acid

(2S)-1-tert-butyloxycarbonyl-4-benzyloxycarbonyl-5-oxoproline tert-butyl ester

(2S,4RS)-tert-butyl N-(tert-butoxycarbonyl)-4-(dimethylaminomethyl)pyroglutamate

L-t-butyl pyroglutamate

Refernces

• 1、 -. "L-Y-METHYLENEGLUTAMINE COMPOUNDS AND METHODS OF USE". Paragraph 0085-0087. . Retrieved 2021/02/12.
• 2、 Chiha, Slim,Spilles, Matthias,Neud?rfl, J?rg-Martin,Schmalz, Hans-Günther. "A Stereoselective Synthesis of the ACE Inhibitor Trandolapril". supporting information. p. 813 - 816. Retrieved 2019/04/25.