2,5-Dioxopyrrolidin-1-yl 1-(tert-butoxycarbonyl)prolinate

Base Information

• Chemical Name: 2,5-Dioxopyrrolidin-1-yl 1-(tert-butoxycarbonyl)prolinate
• CAS No.: 3392-10-7
• Molecular Formula: C14H20 N2 O6
• Molecular Weight: 312.323
• Hs Code.: 2925190090
• DSSTox Substance ID: DTXSID90955510
• Nikkaji Number: J347.943I
• Mol file: 3392-10-7.mol

Synonyms:2,5-dioxopyrrolidin-1-yl 1-(tert-butoxycarbonyl)prolinate;MFCD00069687;Boc-L-Pro-OSu;Oprea1_153813;SCHEMBL357242;DTXSID90955510;EINECS 222-233-9;STK126107;1-O-tert-butyl 2-O-(2,5-dioxopyrrolidin-1-yl) pyrrolidine-1,2-dicarboxylate;AKOS000496062;AKOS022077648;Boc-D-proline N-hydroxysuccinimide ester;Boc-L-proline N-hydroxysuccinimide ester;SY058025;FT-0648839;FT-0663559;N-(TERT-BUTOXYCARBONYL)-L-PROLINE N-HYDROXYSUCCINIMIDE ESTER;tert-Butyl (S)-2-(((2,5-dioxo-1-pyrrolidinyl)oxy)carbonyl)pyrrolidine-1-carboxylate

Chemical Property of 2,5-Dioxopyrrolidin-1-yl 1-(tert-butoxycarbonyl)prolinate

Chemical Property:

• Vapor Pressure: 2.63E-07mmHg at 25°C
• Melting Point: 133-135 °C
• Boiling Point: 421.3°Cat760mmHg
• PKA: -3.96±0.40(Predicted)
• Flash Point: 208.6°C
• PSA: 93.22000
• Density: 1.32g/cm³
• LogP: 0.86890
• Storage Temp.: −20°C
• Solubility.: DMF, Ethanol, Methanol
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 312.13213636
• Heavy Atom Count: 22
• Complexity: 494

Purity/Quality:

99% ^*data from raw suppliers

N-t-Boc-L-proline-N-hydroxysuccinimide Ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCCC1C(=O)ON2C(=O)CCC2=O

Technology Process of 2,5-Dioxopyrrolidin-1-yl 1-(tert-butoxycarbonyl)prolinate

There total 9 articles about 2,5-Dioxopyrrolidin-1-yl 1-(tert-butoxycarbonyl)prolinate 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: 94.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0) → tert-butoxycarbonyl-L-proline N-hydroxysuccinimide ester (3392-10-7)

Guidance literature:

With dicyclohexyl-carbodiimide; In tetrahydrofuran; at 0 ℃;

DOI:10.1007/BF02464272

Reference yield: 89.0%

1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0) + bis(N-hydroxysuccinimide) sulfite (90704-86-2) → tert-butoxycarbonyl-L-proline N-hydroxysuccinimide ester (3392-10-7)

Guidance literature:

With pyridine; at 22 ℃; for 1h;

Reference yield: 82.0%

1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0) + 1,2,2,2-tetrachloroethyl-(N-succinimidyl)carbonate (107960-02-1) → tert-butoxycarbonyl-L-proline N-hydroxysuccinimide ester (3392-10-7)

Guidance literature:

With 4-methyl-morpholine; In tetrahydrofuran; acetonitrile; Ambient temperature;

DOI:10.1021/jo00388a005

upstream raw materials:

1-(tert-butoxycarbonyl)-L-proline

1,2,2,2-tetrachloroethyl-(N-succinimidyl)carbonate

bis(N-hydroxysuccinimide) sulfite

3-[4-(3-chlorophenyl)piperazin-1-yl]propanamine

Downstream raw materials:

(S)-methyl 2-((S)-2-((tert-butoxycarbonyl)amino)propanamido)propanoate

Boc-Pro-Glu(OBzl)-OH

N-tert-butyloxycarbonyl-(2S)-prolyl-glycine benzyl ester

N^α--N^γ-(benzyloxycarbonyl)-L-lysine

Refernces

• 1、 Tereshchenkov, Andrey G.,Dobosz-Bartoszek, Malgorzata,Osterman, Ilya A.,Marks, James,Sergeeva, Vasilina A.,Kasatsky, Pavel,Komarova, Ekaterina S.,Stavrianidi, Andrey N.,Rodin, Igor A.,Konevega, Andrey L.,Sergiev, Petr V.,Sumbatyan, Natalia V.,Mankin, Alexander S.,Bogdanov, Alexey A.,Polikanov, Yury S.. "Binding and Action of Amino Acid Analogs of Chloramphenicol upon the Bacterial Ribosome". . p. 842 - 852. Retrieved 2018/02/26.
• 2、 Gauchot, Vincent,Schmitzer, Andreea R.. "Catalytic anions embedded into avidin: Importance of their chirality and the chiral environment on the stereocontrol of the aldol reaction". . p. 2694 - 2701. Retrieved 2014/04/17.