Carbamic acid, [(1S)-2-(4-fluorophenyl)-1-formylethyl]-, 1,1-dimethylethyl ester

Base Information

• Chemical Name: Carbamic acid, [(1S)-2-(4-fluorophenyl)-1-formylethyl]-, 1,1-dimethylethyl ester
• CAS No.: 135544-90-0
• Molecular Formula: C14H18FNO3
• Molecular Weight: 267.3
• Mol file: 135544-90-0.mol

Synonyms:

Chemical Property of Carbamic acid, [(1S)-2-(4-fluorophenyl)-1-formylethyl]-, 1,1-dimethylethyl ester

Chemical Property:

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Carbamic acid, [(1S)-2-(4-fluorophenyl)-1-formylethyl]-, 1,1-dimethylethyl ester

There total 6 articles about Carbamic acid, [(1S)-2-(4-fluorophenyl)-1-formylethyl]-, 1,1-dimethylethyl ester 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: 99.0%

tert-butyl N-[(1S)-1-[(4-fluorophenyl)methyl]-2-[methoxy(methyl)amino]-2-oxo-ethyl]carbamate (135545-01-6) → (S)-tert-butyl (1-(4-fluorophenyl)-3-oxopropan-2-yl)carbamate (135544-90-0)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 1.5h;

Reference yield: 99.0%

(S)-tert-butyl (1-(4-fluorophenyl)-3-hydroxypropan-2-yl)carbamate (149267-74-3) → (S)-tert-butyl (1-(4-fluorophenyl)-3-oxopropan-2-yl)carbamate (135544-90-0)

Guidance literature:

With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; for 2h;

DOI:10.1002/chem.201700874

Reference yield:

oxalyl dichloride (79-37-8) + (S)-tert-butyl (1-(4-fluorophenyl)-3-hydroxypropan-2-yl)carbamate (149267-74-3) → (S)-tert-butyl (1-(4-fluorophenyl)-3-oxopropan-2-yl)carbamate (135544-90-0)

Guidance literature:

With potassium hydrogen sulphate; triethylamine; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide;

upstream raw materials:

tert-butyl N-[(1S)-1-[(4-fluorophenyl)methyl]-2-[methoxy(methyl)amino]-2-oxo-ethyl]carbamate

Boc-Phe(p-F)

oxalyl dichloride

(S)-tert-butyl (1-(4-fluorophenyl)-3-hydroxypropan-2-yl)carbamate

Downstream raw materials:

(S)-2-Amino-N-[(S)-2-ethylcarbamoyl-1-(4-fluoro-benzyl)-2-hydroxy-ethyl]-3-methyl-butyramide

5-[1,2]Dithiolan-3-yl-pentanoic acid {(S)-1-[(S)-2-ethylcarbamoyl-1-(4-fluoro-benzyl)-2-hydroxy-ethylcarbamoyl]-2-methyl-propyl}-amide

Refernces

• 1、 Sani, Monica,Lazzari, Paolo,Folini, Marco,Spiga, Marco,Zuco, Valentina,De Cesare, Michelandrea,Manca, Ilaria,Dall'Angelo, Sergio,Frigerio, Massimo,Usai, Igor,Testa, Andrea,Zaffaroni, Nadia,Zanda, Matteo. "Synthesis and Superpotent Anticancer Activity of Tubulysins Carrying Non-hydrolysable N-Substituents on Tubuvaline". . p. 5842 - 5850. Retrieved 2017/04/28.
• 2、 Lescop, Cyrille,Herzner, Holger,Siendt, Herve,Bolliger, Reto,Henneboehle, Marco,Weyermann, Philipp,Briguet, Alexandre,Courdier-Fruh, Isabelle,Erb, Michael,Foster, Mark,Meier, Thomas,Magyar, Josef P.,Von Sprecher, Andreas. "Novel cell-penetrating α-keto-amide calpain inhibitors as potential treatment for muscular dystrophy". . p. 5176 - 5181. Retrieved 2007/10/03.