(r)-3-Amino-4-(2,4,5-trifluorophenyl)butanoic acid

Base Information

• Chemical Name: (r)-3-Amino-4-(2,4,5-trifluorophenyl)butanoic acid
• CAS No.: 936630-57-8
• Molecular Formula: C10H10F3NO2
• Molecular Weight: 233.19
• Hs Code.: 2922499990
• European Community (EC) Number: 889-027-4
• UNII: NG2PN5Z4PE
• DSSTox Substance ID: DTXSID60428049
• ChEMBL ID: CHEMBL4981476
• Mol file: 936630-57-8.mol

Synonyms:936630-57-8;(r)-3-amino-4-(2,4,5-trifluorophenyl)butanoic acid;(R)-3-AMINO-4-(2,4,5-TRIFLUOROPHENYL)BUTYRIC ACID;(3R)-3-amino-4-(2,4,5-trifluorophenyl)butanoic Acid;Sitagliptin acid;NG2PN5Z4PE;(3r)-amino-4-(2,4,5-trifluorophenyl)butanoic acid;Sitagliptin Acid Impurity;UNII-NG2PN5Z4PE;SCHEMBL743022;CHEMBL4981476;DTXSID60428049;KEFQQJVYCWLKPL-ZCFIWIBFSA-N;BCP12296;MFCD07363507;AKOS015890555;DS-8908;AC-23933;CS-0012818;A50495;EN300-393286;A900118;(r)-3-amino-4-(2,4,5-trifluorophenyl)butanoicacid;Benzenebutanoic acid, beta-amino-2,4,5-trifluoro-;Q-101368;3-(R)-amino-4-(2,4,5-trifluorophenyl)butanoic acid;BENZENEBUTANOIC ACID, .BETA.-AMINO-2,4,5-TRIFLUORO-;Benzenebutanoic acid, beta-amino-2,4,5-trifluoro-, (betaR)-;benzenebutanoic acid, .beta.-amino-2,4,5-trifluoro-, (.beta.r)-;Sitagliptin Acid;(3R)-3-Amino-4-(2,4,5-trifluorophenyl)butanoic acid;Benzenebutanoic acid, ?-amino-2,4,5-trifluoro-, (?R)-;(?R)-?-Amino-2,4,5-trifluorobenzenebutanoic acid

Chemical Property of (r)-3-Amino-4-(2,4,5-trifluorophenyl)butanoic acid

Chemical Property:

• Vapor Pressure: 8.67E-05mmHg at 25°C
• Melting Point: 217-219 °C(Solv: water (7732-18-5); acetone (67-64-1))
• Refractive Index: 1.513
• Boiling Point: 326.6 °C at 760 mmHg
• PKA: 3.66±0.10(Predicted)
• Flash Point: 151.3 °C
• PSA: 63.32000
• Density: 1.399 g/cm³
• LogP: 2.14870
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 233.06636305
• Heavy Atom Count: 16
• Complexity: 252

Purity/Quality:

98.0%Min ^*data from raw suppliers

(R)-3-Amino-4-(2,4,5-trifluorophenyl)butanoicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=CC(=C1F)F)F)CC(CC(=O)O)N
• Isomeric SMILES: C1=C(C(=CC(=C1F)F)F)C[C@H](CC(=O)O)N

Technology Process of (r)-3-Amino-4-(2,4,5-trifluorophenyl)butanoic acid

There total 68 articles about (r)-3-Amino-4-(2,4,5-trifluorophenyl)butanoic 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: 96.0%

C35H27Cl3F3N3NiO3 → (R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid (936630-57-8) + (R)-N-(2-benzoyl-4-chlorophenyl)-1-[(3,4-dichlorophenyl)methyl]-2-pyrrolidinecarboxamide (1644308-43-9)

Guidance literature:

With hydrogenchloride; In ethanol; at 50 ℃;

DOI:10.1002/anie.201403556

Reference yield: 95.0%

(R)-3-benzoylamino-4-(2,4,5-trifluorophenyl)butanoic acid methyl ester (1402570-02-8) → (R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid (936630-57-8)

Guidance literature:

With hydrogenchloride; In water; Reflux;

Reference yield: 93.2%

(S)-methyl 3-(dibenzylamino)-4-oxo-4-(2,4,5-trifluorophenyl)butanoate (1334630-72-6) → (R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid (936630-57-8)

Guidance literature:

(S)-methyl 3-(dibenzylamino)-4-oxo-4-(2,4,5-trifluorophenyl)butanoate; With palladium 10% on activated carbon; hydrogen; In ethanol; at 25 ℃; for 5h;

With hydrogenchloride; water; pH=5 - 6;

upstream raw materials:

ethyl 3-amino-4-(2,4,5-trifluorophenyl)butanoate

(S)-1-(2,4,5-trifluorophenyl)pent-4-en-2-amine

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

(R)-t-butyl 3-(t-butoxycarbonylamino)-4-(2,4,5-trifluorophenyl)butanoate

Downstream raw materials:

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

(R)-4-[(R)-3-amino-4-(2,4,5-trifluorophenyl)butanoyl]-3-(t-butoxymethyl)piperazin-2-one L-tartrate

sitagliptin

(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、 -. "Preparation method of 1,3-dicarbonyl compound and intermediate of the 1,3-dicarbonyl compound". . . Retrieved 2020/05/02.
• 2、 -. "A west geleg sandbank intermediate biological synthesis method (by machine translation)". Paragraph 0081-0086; 0111-0118. . Retrieved 2019/07/04.