BOC-(R)-3-AMINO-4-(2,4,5-TRIFLUORO-PHENYL)-BUTYRIC ACID

Base Information

• Chemical Name: BOC-(R)-3-AMINO-4-(2,4,5-TRIFLUORO-PHENYL)-BUTYRIC ACID
• CAS No.: 486460-00-8
• Molecular Formula: C15H18F3NO4
• Molecular Weight: 333.307
• Hs Code.: 2942000000
• European Community (EC) Number: 691-120-8
• UNII: 2S9NWB23QS
• DSSTox Substance ID: DTXSID70428050
• Nikkaji Number: J3.263.662D
• Wikidata: Q72448507
• Mol file: 486460-00-8.mol

Synonyms:Benzenebutanoic acid, b-[[(1,1-dimethylethoxy)carbonyl]amino]-2,4,5-trifluoro-,(bR)-;(3R)-3-[(1,1-Dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoicacid;(3R)-3-[(tert-Butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoicacid;(3R)-3-[N-(tert-Butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoicacid;(R)-3-(((tert-Butoxy)carbonyl)amino)-4-(2,4,5-trifluorophenyl)butyricacid;(R)-3-[(tert-Butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid;

Chemical Property of BOC-(R)-3-AMINO-4-(2,4,5-TRIFLUORO-PHENYL)-BUTYRIC ACID

Chemical Property:

• Vapor Pressure: 1.25E-08mmHg at 25°C
• Melting Point: 136-138℃
• Refractive Index: 1.494
• Boiling Point: 443.1 °C at 760 mmHg
• PKA: 4.30±0.10(Predicted)
• Flash Point: 221.8 °C
• PSA: 75.63000
• Density: 1.292 g/cm³
• LogP: 3.40530
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slig
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 333.11879254
• Heavy Atom Count: 23
• Complexity: 427

Purity/Quality:

99%min. ^*data from raw suppliers

(R)-3-((tert-Butoxycarbonyl)amino)-4-(2,4,5-trifluorophenyl)butanoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC(=C(C=C1F)F)F)CC(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](CC1=CC(=C(C=C1F)F)F)CC(=O)O
• Description: Boc-(R) -3-amino-4 -(2,4, 5-trifluorophenyl) butyric acid is an important intermediate for the preparation of sitagliptin. Sitagliptinphosphate is the first dipeptidase -IV(dpp-4) inhibitor approved by FDA in 2006. It is used for the treatment of type II diabetes mellitus. It has obvious hypoglycemic effect when used alone or in combination with metformin and pioglitazone, and it is safe to take, well tolerated, with few adverse reactions.
• Uses: (R)-3-((tert-Butoxycarbonyl)amino)-4-(2,4,5-trifluorophenyl)butanoic Acid has been used as a reactant for the preparation of dipeptidyl peptidase-4 (DPP4) inhibitors for the treatment of type 2 diabetes, such as sitagliptin.

Technology Process of BOC-(R)-3-AMINO-4-(2,4,5-TRIFLUORO-PHENYL)-BUTYRIC ACID

There total 159 articles about BOC-(R)-3-AMINO-4-(2,4,5-TRIFLUORO-PHENYL)-BUTYRIC 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: 99.0%

3-(R)-tert-butoxycarbonylamino-4-(2,4,5-trifluorophenyl)butyric acid methyl ester (881995-73-9) → (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid (486460-00-8,922178-94-7)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; at 20 ℃; for 3h;

DOI:10.1016/j.bmcl.2007.01.111

Reference yield: 98.0%

(R)-tert-butyl (4-hydroxy-1-(2,4,5-trifluorophenyl)butan-2-yl)carbamate (1048703-14-5) → (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid (486460-00-8,922178-94-7)

Guidance literature:

With sodium hypochlorite; sodium chlorite; disodium hydrogenphosphate; sodium dihydrogenphosphate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; In water; acetonitrile; at 38 ℃; for 0.333333h; Solvent;

Reference yield: 94.0%

[3-diazo-2-oxo-1-(2,4,5-trifluoro-benzyl)-propyl]-carbamic acid tert-butyl ester (486460-25-7) → (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid (486460-00-8,922178-94-7)

Guidance literature:

With silver benzoate; In 1,4-dioxane; water; for 1.5h; Sonication;

DOI:10.1016/j.tetasy.2014.06.001

upstream raw materials:

[3-diazo-2-oxo-1-(2,4,5-trifluoro-benzyl)-propyl]-carbamic acid tert-butyl ester

(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

di-tert-butyl dicarbonate

3-(R)-tert-butoxycarbonylamino-4-(2,4,5-trifluorophenyl)butyric acid methyl ester

Downstream raw materials:

(3R)-4-[(3R)-3-(tert-butyloxycarbonylamino)-4-(2,4,5-trifluorophenyl) butanoyl]-3-(2,2,2-trifluoroethyl)-1,4-diazepin-2-one

(R)-[3-oxo-3-(tetrahydropyridazin-1-yl)-1-(2,4,5-trifluorobenzyl)propyl]carbamic acid tert-butyl ester

(R)-[3-[1,2]diazepan-1-yl-3-oxo-1-(2,4,5-trifluorobenzyl)propyl]carbamic acid tert-butyl ester

(R)-[3-oxo-3-pyrazolidin-1-yl-1-(2,4,5-trifluorobenzyl)propyl]carbamic acid tert-butyl ester

Refernces

• 1、 Sudhakaran, Shana,Shinde, Prasad G.,Aratikatla, Eswar K.,Kaulage, Sandeep H.,Rana, Priksha,Parit, Ratan S.,Kavale, Dattatry S.,Senthilkumar, Beeran,Punji, Benudhar. "Nickel-Catalyzed Asymmetric Hydrogenation for the Synthesis of a Key Intermediate of Sitagliptin". supporting information. . Retrieved 2021/12/09.
• 2、 Berthold, Dino,Breit, Bernhard. "Synthesis of (?)-(R)-Sitagliptin by RhI-Catalyzed Asymmetric Hydroamination". supporting information. p. 6247 - 6249. Retrieved 2021/09/25.