(1R,4S,5S,6S)-4-Amino-2-thiabicyclo[3.1.0]hexane-4,6-dicarboxylic acid 2,2-dioxide

Base Information

• Chemical Name: (1R,4S,5S,6S)-4-Amino-2-thiabicyclo[3.1.0]hexane-4,6-dicarboxylic acid 2,2-dioxide
• CAS No.: 635318-11-5
• Molecular Formula: C₇H₉NO₆S
• Molecular Weight: 235.218
• UNII: 531QUG7P9E
• DSSTox Substance ID: DTXSID40212943
• Nikkaji Number: J2.897.724G
• Wikipedia: Pomaglumetad
• Wikidata: Q6460431
• Pharos Ligand ID: 9Q4NBR7KSKSQ
• ChEMBL ID: CHEMBL375611
• Mol file: 635318-11-5.mol

Synonyms:4-aminho-2-thiabicyclo(3.1.0)hexane-4,6-dicarboxylic acid;LY 404039;LY 404040;LY-404039;LY-404040;LY404039;LY404040

Chemical Property of (1R,4S,5S,6S)-4-Amino-2-thiabicyclo[3.1.0]hexane-4,6-dicarboxylic acid 2,2-dioxide

Chemical Property:

• Melting Point: >250 °C(Solv: water (7732-18-5))
• Boiling Point: 600.3±55.0 °C(Predicted)
• PKA: 1.15±0.40(Predicted)
• PSA: 143.14000
• Density: 1.888 g/cm³
• LogP: -0.32280
• Solubility.: insoluble in DMSO; insoluble in EtOH; insoluble in H2O
• XLogP3: -4.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 235.01505818
• Heavy Atom Count: 15
• Complexity: 451

Purity/Quality:

99.99%HPLC ^*data from raw suppliers

LY-404039 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C2C(C2S1(=O)=O)C(=O)O)(C(=O)O)N
• Isomeric SMILES: C1[C@]([C@@H]2[C@H]([C@@H]2S1(=O)=O)C(=O)O)(C(=O)O)N
• Uses: LY 2140023 is a drug developed as a treatment option for schizophrenia. It targets the mGlu2/3 receptor once metabolized.

Technology Process of (1R,4S,5S,6S)-4-Amino-2-thiabicyclo[3.1.0]hexane-4,6-dicarboxylic acid 2,2-dioxide

There total 12 articles about (1R,4S,5S,6S)-4-Amino-2-thiabicyclo[3.1.0]hexane-4,6-dicarboxylic acid 2,2-dioxide 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: 94.0%

(-)-(1'R,4S,5'S,6'S)-2,5-dioxospiro(imidazolidine-4,4'-[2]-thiabicyclo[3.1.0]hexane)-6'-carboxylic acid 2',2'-dioxide (635318-10-4) → LY 404039 (635318-11-5)

Guidance literature:

With phosphoric acid; water; hydrogen bromide; at 130 ℃; for 25h; Large scale reaction;

DOI:10.1021/op100325h

Reference yield:

(1R,4S,5S,6S)-4-amino-2,2-dioxo-2λ6-thia-bicyclo[3.1.0]hexane-4,6-dicarboxylic acid dimethyl ester (635317-62-3) → LY 404039 (635318-11-5)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran;

DOI:10.1021/jm060917u

Reference yield:

4-amino-2-thia-bicyclo[3.1.0]hexane-4,6-dicarboxylic acid dimethyl ester (926291-21-6) → LY 404039 (635318-11-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 6.7 g / tetrahydrofuran / 24 h / 20 °C

2: 89 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 4.5 h / -78 °C

3: 84 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 0 - 20 °C

4: 73 percent / trifluoroacetic acid / 20 °C

5: aq. NaOH / tetrahydrofuran

With sodium hydroxide; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm060917u

upstream raw materials:

(1R,4S,5S,6S)-4-amino-2,2-dioxo-2λ⁶-thia-bicyclo[3.1.0]hexane-4,6-dicarboxylic acid dimethyl ester

4-amino-2-thia-bicyclo[3.1.0]hexane-4,6-dicarboxylic acid dimethyl ester

LY 389795

dimethyl (-)-(1R,4S,5S,6S)-4-(N-tert-butyloxycarbonylamino)-2-thiabicyclo[3.1.0]hexane-4,6-dicarboxylate

Refernces

• 1、 Waser, Mario,Moher, Eric D.,Borders, Sandy S. K.,Hansen, Marvin M.,Hoard, David W.,Laurila, Michael E.,Letourneau, Michael E.,Miller, Richard D.,Phillips, Michael L.,Sullivan, Kevin A.,Ward, Jeffrey A.,Xie, Chaoyu,Bye, Cheryl A.,Leitner, Tanja,Herzog-Krimbacher, Brigitte,Kordian, Marcus,Muellner, Martin. "Process development for a key synthetic intermediate of LY2140023, a clinical candidate for the treatment of schizophrenia". experimental part. p. 1266 - 1274. Retrieved 2012/01/06.