CID 15871347

Base Information

• Chemical Name: CID 15871347
• CAS No.: 77162-51-7
• Molecular Formula: C₆H₁₁NO₂
• Molecular Weight: 129.159
• Hs Code.: 2922499990
• Mol file: 77162-51-7.mol

Synonyms:

Chemical Property of CID 15871347

Chemical Property:

• Vapor Pressure: 0.0012mmHg at 25°C
• Melting Point: 169-170 °C
• Boiling Point: 277.7°C at 760 mmHg
• Flash Point: 121.7°C
• PSA: 63.32000
• Density: 1.064g/cm³
• LogP: 1.06480
• XLogP3: -1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 129.078978594
• Heavy Atom Count: 9
• Complexity: 106

Purity/Quality:

≥99% ^*data from raw suppliers

(R)-Vigabatrin ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CC(CCC(=O)[O-])[NH3+]
• Isomeric SMILES: C=C[C@@H](CCC(=O)[O-])[NH3+]
• Uses: The R-enantiomer of Vigabatrin, a novel antiepileptic The R-enantiomer of Vigabatrin, a novel antiepileptic drug. Antidepressant; antipsychotic; anxiolytic.

Technology Process of CID 15871347

There total 21 articles about CID 15871347 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: 91.0%

(R)-5-vinyl-2-pyrrolidinone (93288-24-5) → (R)-vigabatrin (77162-51-7,68506-86-5)

Guidance literature:

With potassium hydroxide; In water; isopropyl alcohol; for 24h; Heating;

DOI:10.1016/S0040-4020(01)85629-5

Reference yield: 89.0%

(S)-ethyl 4--5-hexenoate (148073-34-1) → (+)-Vigabatrin (74046-07-4,68506-86-5) + (R)-vigabatrin (77162-51-7,68506-86-5)

Guidance literature:

With trimethylsilyl iodide; In dichloromethane; Yields of byproduct given. Title compound not separated from byproducts; a) 0 deg C, 4 h, b) room temperature, 8 h;

DOI:10.1021/jo00058a050

Reference yield: 80.0%

N-<(R)-1-phenylethyl>-(5R)-5-vinyl-2-pyrrolidinone-1-carboxamide → (R)-vigabatrin (77162-51-7,68506-86-5)

Guidance literature:

With barium dihydroxide; In water; isopropyl alcohol; for 12h; Heating;

upstream raw materials:

(S)-ethyl 4--5-hexenoate

(R)-5-vinyl-2-pyrrolidinone

(S)-4-(Benzyl-hydroxy-amino)-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-but-2-ynoic acid methyl ester

(R)-4-tert-Butoxycarbonylamino-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butyric acid methyl ester

Refernces

• 1、 Karumanchi, Kishore,Kumar Natarajan, Senthil,Moturu, Krishna Murthy V. R.,Chavakula, Ramadas,Korupolu, Raghu Babu,Bonige, Kishore Babu. "Resolution of racemic Vigabatrin using tartaric acid". . p. 2221 - 2225. Retrieved 2018/07/21.
• 2、 Dagoneau,Tomassini,Denis,Vallée. "A short synthesis of γ-amino acids from nitrones; synthesis of Vigabatrin". . p. 150 - 154. Retrieved 2007/10/03.