tert-butyl N-[(2S)-1-[(2S,4S)-2-cyano-4-fluoropyrrolidin-1-yl]-3-(2-methylthiazol-4-yl)-1-oxopropan-2-yl]carbamate

Base Information

• Chemical Name: tert-butyl N-[(2S)-1-[(2S,4S)-2-cyano-4-fluoropyrrolidin-1-yl]-3-(2-methylthiazol-4-yl)-1-oxopropan-2-yl]carbamate
• CAS No.: 1580457-14-2
• Molecular Formula: C₁₇H₂₃FN₄O₃S
• Molecular Weight: 382.459
• Mol file: 1580457-14-2.mol

Synonyms:tert-butyl N-[(2S)-1-[(2S,4S)-2-cyano-4-fluoropyrrolidin-1-yl]-3-(2-methylthiazol-4-yl)-1-oxopropan-2-yl]carbamate

Chemical Property of tert-butyl N-[(2S)-1-[(2S,4S)-2-cyano-4-fluoropyrrolidin-1-yl]-3-(2-methylthiazol-4-yl)-1-oxopropan-2-yl]carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl N-[(2S)-1-[(2S,4S)-2-cyano-4-fluoropyrrolidin-1-yl]-3-(2-methylthiazol-4-yl)-1-oxopropan-2-yl]carbamate

There total 2 articles about tert-butyl N-[(2S)-1-[(2S,4S)-2-cyano-4-fluoropyrrolidin-1-yl]-3-(2-methylthiazol-4-yl)-1-oxopropan-2-yl]carbamate 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:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → tert-butyl N-[(2S)-1-[(2S,4S)-2-cyano-4-fluoropyrrolidin-1-yl]-3-(2-methylthiazol-4-yl)-1-oxopropan-2-yl]carbamate (1580457-14-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium hydrogencarbonate / 1,4-dioxane / 24 h / 20 °C

2.1: diethylamino-sulfur trifluoride / dichloromethane / 24 h / -78 - 20 °C / Inert atmosphere

3.1: lithium hydroxide monohydrate / 1,4-dioxane; water / 3 h / 20 °C

4.1: di-tert-butyl dicarbonate; pyridine; ammonium bicarbonate / 1,4-dioxane / 6 h / 20 °C

5.1: 1,3,5-trichloro-2,4,6-triazine / N,N-dimethyl-formamide / 1 h / 20 °C

6.1: acetonitrile / 24 h / 20 °C

7.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.5 h / 20 °C

7.2: 20 h / 20 °C

With pyridine; 1,3,5-trichloro-2,4,6-triazine; lithium hydroxide monohydrate; diethylamino-sulfur trifluoride; di-tert-butyl dicarbonate; sodium hydrogencarbonate; ammonium bicarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.ejmech.2014.01.021

Reference yield:

1-tert-butyl 2-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate (203866-16-4) → tert-butyl N-[(2S)-1-[(2S,4S)-2-cyano-4-fluoropyrrolidin-1-yl]-3-(2-methylthiazol-4-yl)-1-oxopropan-2-yl]carbamate (1580457-14-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: lithium hydroxide monohydrate / 1,4-dioxane; water / 3 h / 20 °C

2.1: di-tert-butyl dicarbonate; pyridine; ammonium bicarbonate / 1,4-dioxane / 6 h / 20 °C

3.1: 1,3,5-trichloro-2,4,6-triazine / N,N-dimethyl-formamide / 1 h / 20 °C

4.1: acetonitrile / 24 h / 20 °C

5.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.5 h / 20 °C

5.2: 20 h / 20 °C

With pyridine; 1,3,5-trichloro-2,4,6-triazine; lithium hydroxide monohydrate; di-tert-butyl dicarbonate; ammonium bicarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In 1,4-dioxane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.ejmech.2014.01.021

upstream raw materials:

L-4-hydroxyproline methyl ester hydrochloride

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