(R)-b-(Boc-amino)-2,5-difluorobenzenebutanoic acid

Base Information

• Chemical Name: (R)-b-(Boc-amino)-2,5-difluorobenzenebutanoic acid
• CAS No.: 486459-98-7
• Molecular Formula: C15H19F2NO4
• Molecular Weight: 315.317
• UNII: GZ7Y2A878J
• Nikkaji Number: J2.163.907I
• Mol file: 486459-98-7.mol

Synonyms:486459-98-7;(R)-b-(Boc-amino)-2,5-difluorobenzenebutanoic acid;Sitagliptin Defuoro IMpurity 4;(3R)-3-[(1,1-Dimethylethoxycarbonyl)amino]-4-(2,5-difluorophenyl)butanoic Acid;(3R)-3-[(tert-Butoxycarbonyl)amino]-4-(2,5-difluorophenyl)butanoic acid;(R)-3-[((tert-Butoxy)carbonyl)amino]-4-(2,5-difluorophenyl)butanoic Acid;GZ7Y2A878J;SCHEMBL1509219;DYAISPAQPPRCQC-LLVKDONJSA-N;MFCD09029663;AKOS015962698;(3R)-4-(2,5-difluorophenyl)-3-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic Acid;BS-17102;CS-0165424;D80588;A899716;(R)-b-(Boc-amino)-2,5-difluorobenzenebutanoicacid;(R)-beta-(Boc-amino)-2,5-difluorobenzenebutanoic acid;3-[(tert-Butoxycarbonyl)amino]-4-(2,5-difluorophenyl)butanoic acid, (3R)-;(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]4-(2,5-difluorophenyl)butanoic acid;(betaR)-beta-[[(1,1-Dimethylethoxy)carbonyl]amino]-2,5-difluorobenzenebutanoic acid;Benzenebutanoic acid, beta-[[(1,1-dimethylethoxy)carbonyl]amino]-2,5-difluoro-, (betaR)-;(R)-3-((tert-butoxycarbonyl)amino)-4-(2,5-difluorophenyl)butanoic acid? (Sitagliptin Impurity pound(c)

Chemical Property of (R)-b-(Boc-amino)-2,5-difluorobenzenebutanoic acid

Chemical Property:

• Boiling Point: 442.9±45.0 °C(Predicted)
• PKA: 4.35±0.10(Predicted)
• PSA: 75.63000
• Density: 1.243±0.06 g/cm3(Predicted)
• LogP: 3.26620
• Storage Temp.: 2-8°C
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 315.12821441
• Heavy Atom Count: 22
• Complexity: 398

Purity/Quality:

98%Min ^*data from raw suppliers

(R)-3-[((tert-Butoxy)carbonyl)amino]-4-(2,5-difluorophenyl)butanoic acid ^*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=C(C=CC(=C1)F)F)CC(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](CC1=C(C=CC(=C1)F)F)CC(=O)O

Technology Process of (R)-b-(Boc-amino)-2,5-difluorobenzenebutanoic acid

There total 20 articles about (R)-b-(Boc-amino)-2,5-difluorobenzenebutanoic 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:

(R,S)-3-[(1,1-dimethylethoxycarbonyl)amino]-1-diazo-4-(2,5-difluoro-phenyl)butan-2-one (486460-03-1) → (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,5-difluorophenyl)butanoic acid (486459-98-7)

Guidance literature:

(R,S)-3-[(1,1-dimethylethoxycarbonyl)amino]-1-diazo-4-(2,5-difluoro-phenyl)butan-2-one; With silver benzoate; N-ethyl-N,N-diisopropylamine; In methanol; at -30 ℃; for 1.5h;

With lithium hydroxide; In tetrahydrofuran; methanol; water; at 50 ℃; for 4h;

Reference yield:

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,5-difluorophenyl)butanoic acid methyl ester (837430-13-4) → (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,5-difluorophenyl)butanoic acid (486459-98-7)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; at 20 ℃; for 16h;

DOI:10.1021/jm0493156

Reference yield:

(R)-3-[(1,1-dimethylethoxycarbonyl)amino]-1-diazo-4-(2,5-difluorophenyl)butan-2-one (837430-12-3) → (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,5-difluorophenyl)butanoic acid (486459-98-7)

Guidance literature:

With silver benzoate; In 1,4-dioxane; at 20 ℃; sonication;

DOI:10.1016/j.bmcl.2004.06.099

upstream raw materials:

(R)-3-[(1,1-dimethylethoxycarbonyl)amino]-1-diazo-4-(2,5-difluorophenyl)butan-2-one

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

(R)-3-Amino-4-(2,5-difluoro-phenyl)-butyric acid methyl ester

di-tert-butyl dicarbonate

Refernces

• 1、 -. "FUSED TRIAZOLE DERIVATIVES AS DIPEPTIDYL PEPTIDASE-IV INHIBITORS FOR THE TREATMENT OR PREVENTION OF DIABETES". Page/Page column 41. . Retrieved 2008/06/13.
• 2、 Angelaud, Remy,Zhong, Yong-Li,Maligres, Peter,Lee, Jaemoon,Askin, David. "Synthesis of a β-amino acid pharmacophore via a β-lactam intermediate". . p. 1949 - 1952. Retrieved 2007/10/03.