cis-1,3-Dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid

Base Information

• Chemical Name: cis-1,3-Dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid
• CAS No.: 51591-75-4
• Molecular Formula: C₁₉H₁₈N₂O₅
• Molecular Weight: 354.362
• European Community (EC) Number: 257-308-5
• Nikkaji Number: J291.072A
• Wikidata: Q76414577
• Mol file: 51591-75-4.mol

Synonyms:51591-75-4;cis-1,3-Dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid;cis-1,3-Dibenzyl-2-oxo-4,5-imidazolidinedicarboxylic Acid;EINECS 257-308-5;C19-H18-N2-O5;cis-1,3-dibenzyl-2-imidazolidone-4,5-dicarboxylic acid;SCHEMBL353717;MFCD07787509;AS-70493;S12227;A924275;cis-1,3-Dibenzyl-2-oxoimidazolidin-4,5-dicarbonsaure;1,3-dibenzyl-cis-4,5-dicarboxy-2-oxotetrahydroimidazole;2-oxo-1,3-dibenzyl-cis-4,5-imidazolidinedicarboxylic acid;cis-1,3-dibenzyl-2-oxo-imidazolidine-4,5-dicarboxylic acid;1,3-Dibenzyl-2-oxoimidazolidine-4alpha,5alpha-dicarboxylic acid;(4R,5S)-1,3-DIBENZYL-2-OXOIMIDAZOLIDINE-4,5-DICARBOXYLIC ACID

Chemical Property of cis-1,3-Dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 170-174 °C(lit.)
• Boiling Point: 654.241°C at 760 mmHg
• PKA: 3.74±0.40(Predicted)
• Flash Point: 349.473°C
• PSA: 98.15000
• Density: 1.426g/cm³
• LogP: 1.90660
• Storage Temp.: Refrigerator
• Solubility.: DMSO, Methanol
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 354.12157168
• Heavy Atom Count: 26
• Complexity: 494

Purity/Quality:

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

cis-1,3-Dibenzyl-2-imidazolidone-4,5-dicarboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CN2C(C(N(C2=O)CC3=CC=CC=C3)C(=O)O)C(=O)O
• Isomeric SMILES: C1=CC=C(C=C1)CN2[C@H]([C@H](N(C2=O)CC3=CC=CC=C3)C(=O)O)C(=O)O
• Uses: cis-1,3-Dibenzyl-2-imidazolidone-4,5-dicarboxylic Acid is a reagent in the total synthesis of Biotin. (B389040), growth factor present in minute amounts in every living cell. Plays an indispensable role in numerous naturally occurring carboxylation reactions. Occurs mainly bound to proteins or polypeptides. The richest sources are liver, kidney, pancreas, yeast, and milk. The biotin content of cancerous tumors is higher than that of normal tissue.

Technology Process of cis-1,3-Dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid

There total 11 articles about cis-1,3-Dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid 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: 95.0%

(4S,5R)-1,3-dibenzyl-5-hydroxymethyl-2-oxoimidazolidine-4-carboxylic acid lactone (87585-00-0) → cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid (51591-75-4,634188-82-2)

Guidance literature:

With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydroxide; at 10 ℃; pH=10;

Reference yield: 87.0%

(3aR,6S,6aS)-1,3-dibenzyl-6-hydroxy-3,3a,6,6a-tetrahydro-1H-furo<3,4-d>imidazole-2,4-dione (129388-92-7) → cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid (51591-75-4,634188-82-2)

Guidance literature:

With sodium chlorite; sodium carbonate; In water; ethyl acetate; at 25 ℃; for 6.5h; or oxidation with Br₂;

DOI:10.1248/cpb.38.882

Reference yield: 77.0%

phosgene (75-44-5) + N,N-dibenzyl-aspartic acid (14464-17-6) → cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid (51591-75-4,634188-82-2)

Guidance literature:

With sodium hydroxide; urea; In water; ethyl acetate;

upstream raw materials:

phosgene

(2R,3S)-2,3-bis(benzylamino)succinic acid

(3aR,6S,6aS)-1,3-dibenzyl-6-hydroxy-3,3a,6,6a-tetrahydro-1H-furo<3,4-d>imidazole-2,4-dione

(4S,5R)-1,3-dibenzyl-1H-furo[3,4-d]imidazole-2,4,6-trione

Downstream raw materials:

(4S,5R)-1,3-dibenzyl-1H-furo[3,4-d]imidazole-2,4,6-trione

(+/-)-1-benzyl-2-oxo-imidazolidine-4r,5c-dicarboxylic acid

dimethyl cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylate

(4S,5R)-1,3-Dibenzyl-2-oxo-imidazolidine-4,5-dicarboxylic acid dipropyl ester

Refernces

• 1、 -. "Synthesis method of biotin intermediate". Paragraph 0040; 0041. . Retrieved 2018/04/03.
• 2、 Chen,Huang,Fu,Cheng,Zhang,Li,Peng. "An efficient and enantioselective synthesis of d-biotin". . p. 2004 - 2008. Retrieved 2007/10/03.