BOC-D-2,4,5-TRIFLUOROPHE

Base Information

• Chemical Name: BOC-D-2,4,5-TRIFLUOROPHE
• CAS No.: 486460-09-7
• Molecular Formula: C14H16F3NO4
• Molecular Weight: 319.281
• Hs Code.: 2924299090
• Mol file: 486460-09-7.mol

Synonyms:(R)-N-(TERT-BUTOXYCARBONYL)-2,4,5-TRIFLUOROPHENYLALANINE;BOC-D-2,4,5-TRIFLUOROPHE;BOC-D-2,4,5-TRIFLUOROPHENYLALANINE;(2R)-2-[(TERT-BUTOXYCARBONYL)AMINO]-3-(2,4,5-TRIFLUOROPHENYL)PROPANOIC ACID

Chemical Property of BOC-D-2,4,5-TRIFLUOROPHE

Chemical Property:

• Boiling Point: 424.7±45.0 °C(Predicted)
• PKA: 3.79±0.14(Predicted)
• PSA: 75.63000
• Density: 1.323±0.06 g/cm3(Predicted)
• LogP: 3.01520
• Storage Temp.: 2-8°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

Boc-D-2,4,5-trifluorophenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of BOC-D-2,4,5-TRIFLUOROPHE

There total 8 articles about BOC-D-2,4,5-TRIFLUOROPHE 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:

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

sitagliptin

[3-(5,6-dihydro-8H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl)-3-oxo-1-(2,4,5-trifluoro-benzyl)-propyl]-carbamic acid tert-butyl ester

(R)-tert-butyl 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-ylcarbamate

Refernces

• 1、 Subbaiah,Haq, Wahajul. "Efficient stereocontrolled synthesis of sitagliptin phosphate". . p. 1026 - 1030. Retrieved 2014/08/18.
• 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.