(S)-tert-butyl 2-(2-carbamoyl-4,4-difluoropyrrolidin-1-yl)-2-oxoethylcarbamate

Base Information

• Chemical Name: (S)-tert-butyl 2-(2-carbamoyl-4,4-difluoropyrrolidin-1-yl)-2-oxoethylcarbamate
• CAS No.: 1448440-48-9
• Molecular Formula: C₁₂H₁₉F₂N₃O₄
• Molecular Weight: 307.297
• Mol file: 1448440-48-9.mol

Synonyms:

Chemical Property of (S)-tert-butyl 2-(2-carbamoyl-4,4-difluoropyrrolidin-1-yl)-2-oxoethylcarbamate

Chemical Property:

• Boiling Point: 524.1±50.0 °C(Predicted)
• Density: 1.30±0.1 g/cm3(Predicted)

Purity/Quality:

97% ^*data from raw suppliers

(S)-tert-Butyl (2-(2-carbamoyl-4,4-difluoropyrrolidin-1-yl)-2-oxoethyl)carbamate 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-tert-butyl 2-(2-carbamoyl-4,4-difluoropyrrolidin-1-yl)-2-oxoethylcarbamate

There total 9 articles about (S)-tert-butyl 2-(2-carbamoyl-4,4-difluoropyrrolidin-1-yl)-2-oxoethylcarbamate 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: 77.0%

BOC-glycine (4530-20-5) + (S)-4,4-difluoropyrrolidine-2-carboxamide hydrochloride (1315053-41-8,426844-51-1) → (S)-tert-butyl 2-(2-carbamoyl-4,4-difluoropyrrolidin-1-yl)-2-oxoethylcarbamate (1448440-48-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; N,N-dimethyl-formamide; for 3h;

Reference yield: 77.0%

BOC-glycine (4530-20-5) + (S)-4,4-difluoropyrrolidine-2-carboxamide trifluoroacetic acid (1448440-46-7) → (S)-tert-butyl 2-(2-carbamoyl-4,4-difluoropyrrolidin-1-yl)-2-oxoethylcarbamate (1448440-48-9)

Guidance literature:

BOC-glycine; With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; N,N-dimethyl-formamide; for 0.166667h;

(S)-4,4-difluoropyrrolidine-2-carboxamide trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide; for 3h;

DOI:10.1021/jm500031w

Reference yield:

(S)-1-tert-butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate (102195-80-2) → (S)-tert-butyl 2-(2-carbamoyl-4,4-difluoropyrrolidin-1-yl)-2-oxoethylcarbamate (1448440-48-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: diethylamino-sulfur trifluoride; ethanol / dichloromethane / 18 h / 20 °C / Inert atmosphere

2.1: potassium hydroxide

3.1: dicyclohexyl-carbodiimide; 1-hydroxy-pyrrolidine-2,5-dione / dichloromethane / 15 - 20 °C

3.2: 0.33 h / 20 °C

4.1: dichloromethane / 1 h

5.1: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane; N,N-dimethyl-formamide / 0.25 h

5.2: 3 h

With 1-hydroxy-pyrrolidine-2,5-dione; ethanol; diethylamino-sulfur trifluoride; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; HATU; potassium hydroxide; In dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

(S)-1-tert-butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate

(2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester

1-tert-butyl 2-methyl (2S)-4,4-difluoropyrrolidine-1,2-dicarboxylate

1-(tert-butoxycarbonyl)-4,4-difluoro-L-proline

Downstream raw materials:

tert-butyl (S)-(2-(2-cyano-4,4-difluoropyrrolidin-1-yl)-2-oxoethyl)carbamate

(S)-1-(2-aminoacetyl)-4,4-difluoropyrrolidine-2-carbonitrile hydrochloride

(S)-1-(2-aminoacetyl)-4,4-difluoropyrrolidine-2-carbonitrile 4-methylbenzenesulfonic acid