1-Benzyl-APDC

Base Information

• Chemical Name: 1-Benzyl-APDC
• CAS No.: 171336-76-8
• Molecular Formula: C13H16N2O4
• Molecular Weight: 264.281
• ChEMBL ID: CHEMBL60238
• DSSTox Substance ID: DTXSID60573467
• Nikkaji Number: J1.126.206F
• Pharos Ligand ID: JXCHUXTB46YK
• Wikidata: Q27070803
• Mol file: 171336-76-8.mol

Synonyms:1-Benzyl-APDC;171336-76-8;CHEMBL60238;GTPL1436;SCHEMBL8061968;DTXSID60573467;BDBM50071161;PD046515;Q27070803;(2R,4R)-4-amino-1-benzylpyrrolidine-2,4-dicarboxylic acid;4-amino-1-(phenylmethyl)pyrrolidine-2,4-dicarboxylic acid;(2R,4R)-4-Amino-1-benzyl-pyrrolidine-2,4-dicarboxylic acid;4-Amino-1-benzyl-pyrrolidine-2,4-dicarboxylic acid(1-benzyl-APDC)

Chemical Property of 1-Benzyl-APDC

Chemical Property:

• XLogP3: -4.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 264.11100700
• Heavy Atom Count: 19
• Complexity: 368

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C(N(CC1(C(=O)O)N)CC2=CC=CC=C2)C(=O)O
• Isomeric SMILES: C1[C@@H](N(C[C@]1(C(=O)O)N)CC2=CC=CC=C2)C(=O)O

Technology Process of 1-Benzyl-APDC

There total 9 articles about 1-Benzyl-APDC 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: 64.0%

(2R,4R)-1-benzyl-2-ethoxycarbonylpyrrolidine-4-spiro-5'-hydantoin (171336-72-4) → (2R,4R) 4-amino-1-(benzyl)-pyrrolidine-2,4-dicarboxylic acid (171336-76-8)

Guidance literature:

With hydrogenchloride; at 130 ℃; for 24h;

DOI:10.1016/0957-4166(95)00209-8

Reference yield: 50.0%

(2R,4R)-4-Amino-1-benzyl-pyrrolidine-2,4-dicarboxylic acid dibenzyl ester (188966-65-6) → (2R,4R) 4-amino-1-(benzyl)-pyrrolidine-2,4-dicarboxylic acid (171336-76-8)

Guidance literature:

With sodium hydroxide; In methanol; Ambient temperature;

DOI:10.1016/S0960-894X(97)00068-1

Reference yield:

(2R,4R) diethyl-1-benzyl-4-(tert-butyloxycarbonylamino) pyrrolidine-2,4-dicarboxylate (174266-81-0) → (2R,4R) 4-amino-1-(benzyl)-pyrrolidine-2,4-dicarboxylic acid (171336-76-8)

Guidance literature:

With hydrogenchloride; sodium hydroxide; Multistep reaction; 1.) Et₂O, 2.) THF, RT;

DOI:10.1016/S0960-894X(98)00352-7

upstream raw materials:

(2R,4R)-1-benzyl-2-ethoxycarbonylpyrrolidine-4-spiro-5'-hydantoin

(2R,4R)-4-Amino-1-benzyl-pyrrolidine-2,4-dicarboxylic acid dibenzyl ester

(2R,4R) diethyl-1-benzyl-4-(tert-butyloxycarbonylamino) pyrrolidine-2,4-dicarboxylate

benzyl chloride

Downstream raw materials:

(2R,4R)-4-amino-4-carboxyproline

(2R,4R)-1-benzyl-4-tert-butoxycarbonylamino-pyrrolidine-2,4-dicarboxylic acid dimethyl ester

(2R,4R)-4-amino-1-benzyl-pyrrolidine-2,4-dicarboxylic acid dimethyl ester

Refernces

• 1、 Tueckmantel, Werner,Kozikowski, Alan P.,Wang, Shaomeng,Pshenichkin, Sergey,Wroblewski, Jarda T.. "Synthesis, molecular modeling, and biology of the 1-benzyl derivative of APDC - an apparent mGluR6 selective ligand". . p. 601 - 606. Retrieved 2007/10/03.
• 2、 Tanaka,Sawanishi. "Asymmetric syntheses of all four isomers of 4-amino-4-carboxyproline: Novel conformationally restricted glutamic acid analogues". . p. 1641 - 1656. Retrieved 2007/10/02.