(R)-2-(tert-butoxycarbonylamino)-3-(2,4,5-trifluorophenyl)propanoic acid

Base Information

• Chemical Name: (R)-2-(tert-butoxycarbonylamino)-3-(2,4,5-trifluorophenyl)propanoic acid
• CAS No.: 1367740-01-9
• Molecular Formula: C₁₄H₁₆F₃NO₄
• Molecular Weight: 319.281
• Mol file: 1367740-01-9.mol

Synonyms:

Chemical Property of (R)-2-(tert-butoxycarbonylamino)-3-(2,4,5-trifluorophenyl)propanoic acid

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

2-{[(tert-Butoxy)carbonyl]amino}-3-(2,4,5-trifluorophenyl)propanoic acid 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-(tert-butoxycarbonylamino)-3-(2,4,5-trifluorophenyl)propanoic acid

There total 8 articles about (R)-2-(tert-butoxycarbonylamino)-3-(2,4,5-trifluorophenyl)propanoic acid 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: 100.0%

di-tert-butyl dicarbonate (24424-99-5) + (3R,6R)-1,4-bis[(R)-1-phenylethyl]-3,6-bis(2,4,5-trifluoro benzyl)piperazine-2,5-dione → (R)-2-(tert-butoxycarbonylamino)-3-(2,4,5-trifluorophenyl)propanoic acid (486460-09-7,1367740-01-9,324028-27-5)

Guidance literature:

(3R,6R)-1,4-bis[(R)-1-phenylethyl]-3,6-bis(2,4,5-trifluoro benzyl)piperazine-2,5-dione; With water; hydrogen iodide; for 3h; Reflux;

di-tert-butyl dicarbonate; With sodium carbonate; In 1,4-dioxane; water; at 0 - 20 ℃; Alkaline conditions;

DOI:10.1016/j.tetasy.2014.06.001

Reference yield:

(R)-methyl 2-((tert-butoxycarbonyl)amino)-3-(2,4,5-trifluorophenyl)propanoate (486460-08-6) → (R)-2-(tert-butoxycarbonylamino)-3-(2,4,5-trifluorophenyl)propanoic acid (486460-09-7,1367740-01-9,324028-27-5)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/jm0493156

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (R)-2-(tert-butoxycarbonylamino)-3-(2,4,5-trifluorophenyl)propanoic acid (486460-09-7,1367740-01-9,324028-27-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: aq. HCl / acetonitrile / 72 h / 20 °C

1.2: 2.41 g / triethylamine / CH₂Cl₂ / 16 h / 20 °C

2.1: aq. LiOH / tetrahydrofuran / 20 °C

With hydrogenchloride; lithium hydroxide; In tetrahydrofuran; acetonitrile;

DOI:10.1021/jm0493156

upstream raw materials:

(R)-methyl 2-((tert-butoxycarbonyl)amino)-3-(2,4,5-trifluorophenyl)propanoate

di-tert-butyl dicarbonate

2,4,5-trifluorobenzyl bromide

(2S,5R)-2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-(2',4',5'-trifluorobenzyl)-pyrazine

Downstream raw materials:

sitagliptin phosphate

Refernces

• 1、 -. "BETA-AMINO HETEROCYCLIC DIPEPTIDYL PEPTIDASE INHIBITORS FOR THE TREATMENT OR PREVENTION OF DIABETES". Paragraph 0178. . Retrieved 2015/12/30.
• 2、 Kim, Dooseop,Wang, Liping,Beconi, Maria,Eiermann, George J.,Fisher, Michael H.,He, Huaibing,Hickey, Gerard J.,Kowalchick, Jennifer E.,Leiting, Barbara,Lyons, Kathryn,Marsilio, Frank,McCann, Margaret E.,Patel, Reshma A.,Petrov, Aleksandr,Scapin, Giovanna,Patel, Sangita B.,Roy, Ranabir Sinha,Wu, Joseph K.,Wyvratt, Matthew J.,Zhang, Bei B.,Zhu, Lan,Thornberry, Nancy A.,Weber, Ann E.. "(2R)-4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a] pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine: A potent, orally active dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes". . p. 141 - 151. Retrieved 2007/10/03.