(S)-Benzyl (2,5-dioxopyrrolidin-3-yl)carbamate

Base Information

• Chemical Name: (S)-Benzyl (2,5-dioxopyrrolidin-3-yl)carbamate
• CAS No.: 60846-91-5
• Molecular Formula: C12H12N2O4
• Molecular Weight: 248.238
• Hs Code.: 2925190090
• DSSTox Substance ID: DTXSID20435375
• Wikidata: Q76415082
• ChEMBL ID: CHEMBL26221
• Mol file: 60846-91-5.mol

Synonyms:(S)-3-N-Cbz-amino-succinimide;60846-91-5;(S)-Benzyl (2,5-dioxopyrrolidin-3-yl)carbamate;Benzyl N-[(3S)-2,5-dioxopyrrolidin-3-yl]carbamate;(phenylmethyl) ~{N}-[(3~{S})-2,5-bis(oxidanylidene)pyrrolidin-3-yl]carbamate;CHEMBL26221;SCHEMBL5180974;DTXSID20435375;(s)-(2,5-dioxo-pyrrolidin-3-yl)-carbamic acid benzyl ester;MFCD05864630;AKOS015912734;AS-38719;CS-0149748;(S)-benzyl(2,5-dioxopyrrolidin-3-yl)carbamate;Q-102891;JP5

Chemical Property of (S)-Benzyl (2,5-dioxopyrrolidin-3-yl)carbamate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.59
• Boiling Point: 515.096 °C at 760 mmHg
• PKA: 8.79±0.50(Predicted)
• Flash Point: 265.321 °C
• PSA: 84.50000
• Density: 1.354 g/cm³
• LogP: 1.04760
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 248.07970687
• Heavy Atom Count: 18
• Complexity: 350

Purity/Quality:

98%Min ^*data from raw suppliers

(S)-3-N-Cbz-aminosuccinimide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(=O)NC1=O)NC(=O)OCC2=CC=CC=C2
• Isomeric SMILES: C1[C@@H](C(=O)NC1=O)NC(=O)OCC2=CC=CC=C2

Technology Process of (S)-Benzyl (2,5-dioxopyrrolidin-3-yl)carbamate

There total 6 articles about (S)-Benzyl (2,5-dioxopyrrolidin-3-yl)carbamate 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: 74.0%

N-(benzyloxycarbonyl)asparagine methyl ester (4668-37-5) → 3-(S)-N-benzyloxycarbonylaminopyrrolidine-2,5-dione (60846-91-5)

Guidance literature:

With hydrogenchloride; In water; for 0.5h;

Reference yield: 25.0%

N-(benzyloxycarbonyl)asparagine methyl ester (4668-37-5) + butan-1-ol (71-36-3) → 3-(S)-N-benzyloxycarbonylaminopyrrolidine-2,5-dione (60846-91-5) + (S)-butyl 4-amino-2-(benzyloxycarbonylamino)-4-oxobutanoate

Guidance literature:

With C₁₂H₆F₁₈O₁₃Zn₄; In di-isopropyl ether; for 18h; Reflux; Inert atmosphere;

DOI:10.1055/s-0031-1290096

Reference yield:

→ 3-(S)-N-benzyloxycarbonylaminopyrrolidine-2,5-dione (60846-91-5)

Guidance literature:

With sodium hydroxide; Behandeln der Reaktionsloesung mit wss. HCl;

DOI:10.1021/ja01638a047

upstream raw materials:

N-(benzyloxycarbonyl)asparagine methyl ester

benzyl chloroformate

butan-1-ol

Downstream raw materials:

(3S)-3-(methylamino)pyrrolidine dihydrochloride

(S)-(1-benzyl-2,5-dioxo-pyrrolidin-3-yl)carbamic acid benzyl ester

N-(benzyloxycarbonyl)-L-asparaginamide

Refernces

• 1、 Maegawa, Yusuke,Agura, Kazushi,Hayashi, Yukiko,Ohshima, Takashi,Mashima, Kazushi. "Transesterification of α-amino esters catalyzed by a tetranuclear zinc cluster: Zn4(OCOCF3)6O". supporting information; experimental part. p. 137 - 141. Retrieved 2012/02/03.
• 2、 Briere, Jean-Francois,Charpentier, Patricia,Dupas, Georges,Queguiner, Guy,Bourguignon, Jean. "Regioselective reductions of various 3-aminosuccinimides; application to the synthesis of two heterocyclic systems". . p. 2075 - 2086. Retrieved 2007/10/03.