(1S,2S,5R,6S)-2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid

Base Information

• Chemical Name: (1S,2S,5R,6S)-2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid
• CAS No.: 176199-48-7
• Molecular Formula: C8H11NO4
• Molecular Weight: 185.18
• UNII: ONU5A67T2S
• DSSTox Substance ID: DTXSID40170094
• Nikkaji Number: J812.964I
• Wikipedia: Eglumetad
• Wikidata: Q5348096
• NCI Thesaurus Code: C76505
• Pharos Ligand ID: VJZ2MKQQ21XF
• ChEMBL ID: CHEMBL8759
• Mol file: 176199-48-7.mol

Synonyms:(+)-(1S,2S,5R,6S)-2-aminobicyclo(3.1.0)hexane-2,6-dicarboxylic acid;2-aminobicyclo(3.1.0)hexane-2,6-dicarboxylic acid;eglumetad;LY 314582;LY 354740;LY 366563;LY-314582;LY-354740;LY-366563;LY314582;LY354740;LY366563

Chemical Property of (1S,2S,5R,6S)-2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid

Chemical Property:

• Vapor Pressure: 1.06E-06mmHg at 25°C
• Melting Point: 270-271 °C
• Refractive Index: 1.619
• Boiling Point: 376.4 °C at 760 mmHg
• PKA: 2.06±0.40(Predicted)
• Flash Point: 181.4 °C
• PSA: 100.62000
• Density: 1.569 g/cm³
• LogP: 0.20940
• Storage Temp.: Store at +4°C
• XLogP3: -3.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 185.06880783
• Heavy Atom Count: 13
• Complexity: 290

Purity/Quality:

99% ^*data from raw suppliers

LY 354740 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(C2C1C2C(=O)O)(C(=O)O)N
• Isomeric SMILES: C1C[C@]([C@H]2[C@@H]1[C@@H]2C(=O)O)(C(=O)O)N
• Uses: Treatment ofgeneral anxiety disorders and smoking cessation (metabotropic glutamate agonist). LY 354740 is a highly selective and potent agonist of group II mGluR.

Technology Process of (1S,2S,5R,6S)-2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid

There total 19 articles about (1S,2S,5R,6S)-2-aminobicyclo[3.1.0]hexane-2,6-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: 85.0%

(1S,2S,5R,6S)-ethyl 2-spirohydantoin-bicyclo[3.1.0]hexane-6-carboxylate (188885-88-3) → eglumetad (176199-48-7,176027-90-0,176199-49-8,177317-28-1,207553-80-8,597540-64-2)

Guidance literature:

(1S,2S,5R,6S)-ethyl 2-spirohydantoin-bicyclo[3.1.0]hexane-6-carboxylate; With sodium hydroxide; for 28h; Reflux;

With hydrogenchloride; In water; at 0 - 20 ℃; for 3h; pH=3;

DOI:10.1016/j.tetasy.2010.04.051

Reference yield: 64.0%

(1S,2S,5R,6S)-2-Acetylamino-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid dimethyl ester (219762-29-5) → eglumetad (176199-48-7,176027-90-0,176199-49-8,177317-28-1,207553-80-8,597540-64-2)

Guidance literature:

With hydrogenchloride; Dowex 50WX₈-100; Heating;

DOI:10.1016/S0040-4039(98)02092-9

Reference yield:

C15H20O5 (188885-69-0) → eglumetad (176199-48-7,176027-90-0,176199-49-8,177317-28-1,207553-80-8,597540-64-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 94 percent / LiHMDS / tetrahydrofuran / -78 °C

2: 84 percent / NaN₃, 18-Crown-6, DBU / 6 h / Ambient temperature

3: 71 percent / H₂ / Pd/C / ethyl acetate / 18 h / 1551.44 Torr

4: 75 percent / TEA / CH₂Cl₂

5: 90 percent / TFA / H₂O

6: 79 percent

7: 40 percent / 5 h / 170 - 180 °C / sealed tube

8: 80 percent / H₂ / Pd/C

9: 64 percent / HCl, Dowex 50WX₈-100 / Heating

With hydrogenchloride; sodium azide; Dowex 50WX₈-100; 18-crown-6 ether; TEA; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate;

DOI:10.1016/S0040-4039(98)02092-9

upstream raw materials:

(1S,2S,5R,6S)-ethyl 2-spirohydantoin-bicyclo[3.1.0]hexane-6-carboxylate

(1S,2S,5R,6S)-2-Acetylamino-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid dimethyl ester

(1S,2S,5R,6S)-2-Amino-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 6-methyl ester

(2aR,2bR,4aS,4bS)-2-Oxo-hexahydro-1-aza-cyclopropa[cd]pentalene-4a-carboxylic acid methyl ester

Downstream raw materials:

(1S,2S,5R,6S)-2-Amino-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid dimethyl ester

(1S,2S,5R,6S)-2-[(2'S)-(2'-tert-butoxycarbonylamino)-propionyl]amino-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid

(1S,2S,5R,6S)-2-tert-butoxycarbonylaminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid 6-methyl ester

(1S,2S,5R,6S)-2-[(2'S)-(2',6'-bis(tert-butoxycarbonyl)amino)hexanoyl]aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid dimethyl ester

Refernces

• 1、 Ohfune, Yasufumi,Demura, Takashi,Iwama, Seiji,Matsuda, Hiromi,Namba, Kosuke,Shimamoto, Keiko,Shinada, Tetsuro. "Stereocontrolled synthesis of a potent agonist of group II metabotropic glutamate receptors, (+)-LY354740, and its related derivatives". . p. 5431 - 5434. Retrieved 2007/10/03.
• 2、 Dominguez, Carmen,Ezquerra, Jesus,Prieto, Lourdes,Espada, Modesta,Pedregal, Carmen. "Asymmetric synthesis of (+)-2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (LY354740)". . p. 511 - 514. Retrieved 2007/10/03.