(S)-1-(2-Chloroacetyl)pyrrolidine-2-carboxaMide

Base Information

• Chemical Name: (S)-1-(2-Chloroacetyl)pyrrolidine-2-carboxaMide
• CAS No.: 214398-99-9
• Molecular Formula: C7H11ClN2O2
• Molecular Weight: 190.63
• Hs Code.: 2933990090
• Mol file: 214398-99-9.mol

Synonyms:2-Pyrrolidinecarboxamide,1-(chloroacetyl)-, (2S)- (9CI);

Chemical Property of (S)-1-(2-Chloroacetyl)pyrrolidine-2-carboxaMide

Chemical Property:

• Melting Point: 133-137℃ (isopropyl ether )
• Boiling Point: 442.5±45.0 °C(Predicted)
• PKA: 15.56±0.20(Predicted)
• PSA: 63.40000
• Density: 1.353±0.06 g/cm3(Predicted)
• LogP: 0.33970
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Chloroform (Slightly, Sonicated), DMSO (Slightly), Methanol (Very Slightly)

Purity/Quality:

99% ^*data from raw suppliers

(S)-1-(2-Chloroacetyl)pyrrolidine-2-carboxamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (S)-1-(2-Chloroacetyl)pyrrolidine-2-carboxamide is used in the synthesis of Vildagliptin (V305000), an oral anti-diabetic drug, and its impurities (H971380) (Impurity A).

Technology Process of (S)-1-(2-Chloroacetyl)pyrrolidine-2-carboxaMide

There total 5 articles about (S)-1-(2-Chloroacetyl)pyrrolidine-2-carboxaMide 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: 96.3%

chloroacetyl chloride (79-04-9) + L-prolinamide (7531-52-4) → (S)-1-(2-chloroacetyl) pyrrolidine-2-carboxamide (214398-99-9)

Guidance literature:

With triethylamine; In dichloromethane; at 5 ℃; for 2h; Reagent/catalyst; Inert atmosphere;

Reference yield: 84.0%

(S)-1-(2-chloroacetyl)pyrrolidine-2-carboxylic acid (23500-10-9) → (S)-1-(2-chloroacetyl) pyrrolidine-2-carboxamide (214398-99-9)

Guidance literature:

With pyridine; di-tert-butyl dicarbonate; ammonium bicarbonate; In acetonitrile; at 20 ℃; for 1.5h; Inert atmosphere;

DOI:10.14233/ajchem.2014.16018

Reference yield:

C7H9Cl2NO2 → (S)-1-(2-chloroacetyl) pyrrolidine-2-carboxamide (214398-99-9)

Guidance literature:

With ammonia; In dichloromethane; for 2h;

upstream raw materials:

chloroacetyl chloride

L-prolinamide

L-proline

(S)-1-(2-chloroacetyl)pyrrolidine-2-carboxylic acid

Downstream raw materials:

(S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile

(S)-1-[2-(3-hydroxyadamantan-1-ylamino)acetyl]pyrrolidine-2-carboxylic acid amide

Refernces

• 1、 Fang, Yuanying,Zhang, Shaokun,Wu, Wenting,Liu, Yanhua,Yang, Juan,Li, Yuyuan,Li, Min,Dong, Huanhuan,Jin, Yi,Liu, Ronghua,Yang, Zunhua. "Design and synthesis of tetrahydropyridopyrimidine derivatives as dual GPR119 and DPP-4 modulators". . . Retrieved 2019/11/13.
• 2、 -. "Vildagliptin related substance and preparation method thereof". Paragraph 0064; 0065; 0066; 0067; 0068; 0085-0089. . Retrieved 2019/06/12.