Benzyl (S)-2-(((2,5-dioxo-1-pyrrolidinyl)oxy)carbonyl)pyrrolidine-1-carboxylate

Base Information

• Chemical Name: Benzyl (S)-2-(((2,5-dioxo-1-pyrrolidinyl)oxy)carbonyl)pyrrolidine-1-carboxylate
• CAS No.: 3397-33-9
• Molecular Formula: C17H18 N2 O6
• Molecular Weight: 346.34
• Hs Code.: 2925190090
• DSSTox Substance ID: DTXSID60955547
• Nikkaji Number: J2.236.417K
• Mol file: 3397-33-9.mol

Synonyms:2,5-dioxopyrrolidin-1-yl 1-[(benzyloxy)carbonyl]prolinate;Benzyl (S)-2-(((2,5-dioxo-1-pyrrolidinyl)oxy)carbonyl)pyrrolidine-1-carboxylate;Z-L-Pro-OSu;Oprea1_837609;SCHEMBL9276822;DTXSID60955547;EINECS 222-255-9;STK535818;1-O-benzyl 2-O-(2,5-dioxopyrrolidin-1-yl) pyrrolidine-1,2-dicarboxylate;AKOS005466892;FT-0771943

Chemical Property of Benzyl (S)-2-(((2,5-dioxo-1-pyrrolidinyl)oxy)carbonyl)pyrrolidine-1-carboxylate

Chemical Property:

• Vapor Pressure: 3.24E-10mmHg at 25°C
• Melting Point: 88-90 °C
• Boiling Point: 502.2°Cat760mmHg
• Flash Point: 257.5°C
• PSA: 93.22000
• Density: 1.4g/cm³
• LogP: 1.27060
• Storage Temp.: -15°C
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 346.11648630
• Heavy Atom Count: 25
• Complexity: 541

Purity/Quality:

99% ^*data from raw suppliers

Z-L-proline N-hydroxysuccinimide ester ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CC(N(C1)C(=O)OCC2=CC=CC=C2)C(=O)ON3C(=O)CCC3=O

Technology Process of Benzyl (S)-2-(((2,5-dioxo-1-pyrrolidinyl)oxy)carbonyl)pyrrolidine-1-carboxylate

There total 4 articles about Benzyl (S)-2-(((2,5-dioxo-1-pyrrolidinyl)oxy)carbonyl)pyrrolidine-1-carboxylate 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: 97.0%

1,2,2,2-tetrachloroethyl-(N-succinimidyl)carbonate (107960-02-1) + N-Benzyloxycarbonyl-L-proline (1148-11-4) → Z-proline N-hydroxysuccinimide ester (3397-33-9)

Guidance literature:

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

DOI:10.1021/jo00388a005

Reference yield: 87.0%

bis(N-hydroxysuccinimide) sulfite (90704-86-2) + N-Benzyloxycarbonyl-L-proline (1148-11-4) → Z-proline N-hydroxysuccinimide ester (3397-33-9)

Guidance literature:

With pyridine; In acetonitrile; at 20 ℃; for 1.5h; further solvent, base;

DOI:10.1007/BF01141728

Reference yield: 77.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + N-Benzyloxycarbonyl-L-proline (1148-11-4) → Z-proline N-hydroxysuccinimide ester (3397-33-9)

Guidance literature:

With N-ethylmorpholine;; benzotriazol-1-ol; In dichloromethane; 1) 0 deg C, 2 h, 2) overnight, r.t.;

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

N-Benzyloxycarbonyl-L-proline

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

bis(N-hydroxysuccinimide) sulfite

Downstream raw materials:

N-(N-benzyloxycarbonyl-L-prolyl)-p-bis(2-hydroxyethyl)amino-L-phenylalanine benzyl ester

N^α-Cbz-Pro-SH

Cbz-Pro-Hyp-Gly-OBn

(S)-benzyl 2-(benzylcarbamoyl)pyrrolidine-1-carboxylate

Refernces

• 1、 Altava, Belén,Isabel Burguete,Carbó, Noèlia,Luis, Santiago V.,Martí-Centelles, Vicente,Vicent, Cristian. "Bis(amino amides) derived from natural amino acids as chiral receptors for N-protected dicarboxylic amino acids". . p. 72 - 79. Retrieved 2013/02/22.
• 2、 Griffin, Martin,Mongeot, Alexandre,Collighan, Russell,Saint, Robert E.,Jones, Richard A.,Coutts, Ian G.C.,Rathbone, Daniel L.. "Synthesis of potent water-soluble tissue transglutaminase inhibitors". scheme or table. p. 5559 - 5562. Retrieved 2009/05/30.