(S)-Di-tert-butyl 4-oxopyrrolidine-1,2-dicarboxylate

Base Information

• Chemical Name: (S)-Di-tert-butyl 4-oxopyrrolidine-1,2-dicarboxylate
• CAS No.: 166410-05-5
• Molecular Formula: C14H23NO5
• Molecular Weight: 285.34
• Hs Code.: 2933990090
• European Community (EC) Number: 807-593-2
• DSSTox Substance ID: DTXSID70463123
• Nikkaji Number: J1.106.825A
• Wikidata: Q72499176
• Mol file: 166410-05-5.mol

Synonyms:166410-05-5;(S)-Di-tert-butyl 4-oxopyrrolidine-1,2-dicarboxylate;N-Boc-4-oxo-L-proline tert-butyl ester;ditert-butyl (2S)-4-oxopyrrolidine-1,2-dicarboxylate;BOC-4-OXO-L-PROLINE TERT-BUTYL ESTER;di-tert-butyl (S)-4-oxopyrrolidine-1,2-dicarboxylate;1,2-Pyrrolidinedicarboxylic acid, 4-oxo-, 1,2-bis(1,1-dimethylethyl) ester, (2S)-;MFCD06797013;MPNWQUWKRDADHK-JTQLQIEISA-N;EC 807-593-2;SCHEMBL875282;DTXSID70463123;(S)-4-Oxopyrrolidine-1,2-dicarboxylic acid di-tert-butyl ester;AM9721;ZB1689;AKOS016003352;CS-W010024;DS-16683;N-Boc-4-oxo-L-proline tert-butyl ester, 97%;P18635;A850872;(S)-Di-tert-butyl4-oxopyrrolidine-1,2-dicarboxylate;Di-tert-butyl (2S)-4-oxopyrrolidine-1,2-dicarboxylate;N-t-BOC-4-Oxo-L-proline tert-butyl ester, AldrichCPR;1-(tert-butyloxycarbonyl)-4-oxo-L-proline tert-butyl ester;1,2-Pyrrolidinedicarboxylicacid,4-oxo-,1,2-bis(1,1-dimethylethyl)ester,(2S)-

Chemical Property of (S)-Di-tert-butyl 4-oxopyrrolidine-1,2-dicarboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 64-67 °C
• Refractive Index: 1.516
• Boiling Point: 366.7 ºC at 760 mmHg
• PKA: -3.86±0.40(Predicted)
• Flash Point: 175.6 ºC
• PSA: 72.91000
• Density: 1.138 g/cm³
• LogP: 1.84450
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• XLogP3: 1.6
• 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:

99.9% ^*data from raw suppliers

Boc-4-oxo-L-proline tert-butyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)C1CC(=O)CN1C(=O)OC(C)(C)C
• Isomeric SMILES: CC(C)(C)OC(=O)[C@@H]1CC(=O)CN1C(=O)OC(C)(C)C

Technology Process of (S)-Di-tert-butyl 4-oxopyrrolidine-1,2-dicarboxylate

There total 7 articles about (S)-Di-tert-butyl 4-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: 92.74%

BOC-Hyp-OtBu (170850-75-6) → tert-butyl Nα-Boc-4-keto-L-prolinate (166410-05-5)

Guidance literature:

With 4-methylmorpholine N-oxide; In dichloromethane; at 20 ℃; for 1.5h; Reagent/catalyst;

Reference yield: 78.0%

N-tert-butoxycarbonyl-4-oxo-L-proline (84348-37-8) + tert-butyl alcohol (75-65-0) → tert-butyl Nα-Boc-4-keto-L-prolinate (166410-05-5)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; for 3h; Ambient temperature;

DOI:10.1016/0040-4020(95)00135-U

Reference yield: 69.8%

tert-butyl methyl ether (1634-04-4) + N-tert-butoxycarbonyl-4-oxo-L-proline (84348-37-8) → tert-butyl Nα-Boc-4-keto-L-prolinate (166410-05-5)

Guidance literature:

With dmap; di-tert-butyl dicarbonate; for 2h; Reflux;

upstream raw materials:

N-tert-butoxycarbonyl-4-oxo-L-proline

tert-butyl alcohol

BOC-Hyp-OtBu

di-tert-butyl dicarbonate

Downstream raw materials:

tert-butyl N^α-Boc-cis-4-hydroxy-4-phenyl-L-prolinate

tert-butyl (2S,4S)-[3,3-²H₂]-N-tert-butoxycarbonyl-4-O-para-toluenesulfonyloxyprolinate

tert-butyl (2S,3R,4S)-[3-²H₁]-N-tert-butoxycarbonyl-4-O-para-toluenesulfonyloxyprolinate

tert-butyl (2S,3S,4S)-[3-²H₁]-N-tert-butoxycarbonyl-4-O-para-toluenesulfonyloxyprolinate