(S)-2-((tert-Butoxycarbonyl)amino)-3-(4-(trifluoromethyl)phenyl)propanoic acid

Base Information

• Chemical Name: (S)-2-((tert-Butoxycarbonyl)amino)-3-(4-(trifluoromethyl)phenyl)propanoic acid
• CAS No.: 114873-07-3
• Molecular Formula: C₁₅H₁₈F₃NO₄
• Molecular Weight: 333.307
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID00427319
• Nikkaji Number: J713.217D
• Mol file: 114873-07-3.mol

Synonyms:114873-07-3;Boc-L-4-Trifluoromethylphenylalanine;(S)-2-((tert-Butoxycarbonyl)amino)-3-(4-(trifluoromethyl)phenyl)propanoic acid;N-BOC-4-(Trifluoromethyl)-L-phenylalanine;Boc-Phe(4-CF3)-OH;Boc-4-Trifluoromethyl-L-Phenylalanine;Boc-4-(trifluoromethyl)-L-phenylalanine;n-boc-4-trifluoromethyl-l-phenylalanine;(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[4-(trifluoromethyl)phenyl]propanoic acid;L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-4-(trifluoromethyl)-;N-(tert-Butoxycarbonyl)-4-(trifluoromethyl)-L-phenylalanine;(S)-2-(tert-butoxycarbonylamino)-3-(4-(trifluoromethyl)phenyl)propanoic acid;MFCD00797557;SCHEMBL441305;4-(TRIFLUOROMETHYL)-L-PHENYLALANINE,BOC PROTECTED;DTXSID00427319;AKOS015836550;AC-9982;AM83501;CS-W011939;HY-W011223;AS-15599;PD196808;B4369;A50150;Boc-Phe(4-CF3)-OH, >=98.0% (TLC);EN300-2010705;A803262;J-003146;N-(tert-butoxycarbonyl)-4-(trifluoromethyl)phenylalanine;N-(tert-Butoxycarbonyl)-4-trifluoromethyl-L-phenylalanine;4-(TRIFLUOROMETHYL)-D-PHENYLALANINE, N-BOC PROTECTED;N-[(1,1-dimethylethoxy)carbonyl]-4-(trifluoromethyl)-L-phenylalanine;(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-[4-(trifluoromethyl)phenyl]propanoic acid

Chemical Property of (S)-2-((tert-Butoxycarbonyl)amino)-3-(4-(trifluoromethyl)phenyl)propanoic acid

Chemical Property:

• Vapor Pressure: 3.29E-08mmHg at 25°C
• Melting Point: 118-137°C
• Refractive Index: 1.487
• Boiling Point: 431.4 °C at 760 mmHg
• PKA: 3.76±0.10(Predicted)
• Flash Point: 214.7 °C
• PSA: 75.63000
• Density: 1.271 g/cm³
• LogP: 3.61670
• Storage Temp.: Keep Cold
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 333.11879254
• Heavy Atom Count: 23
• Complexity: 423

Purity/Quality:

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

Boc-4-Trifluoromethyl-L-phenylalanine 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC=C(C=C1)C(F)(F)F)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC1=CC=C(C=C1)C(F)(F)F)C(=O)O
• Uses: N-(tert-Butoxycarbonyl)-4-trifluoromethyl-L-phenylalanine is a useful pharmaceutical intermediate. It is used in the preparation of ring substituted phenylalanines and tryptophans. Also Used in the preparation of proline derivatives with inhibitory action against dipeptidyl peptidase IV.

Technology Process of (S)-2-((tert-Butoxycarbonyl)amino)-3-(4-(trifluoromethyl)phenyl)propanoic acid

There total 3 articles about (S)-2-((tert-Butoxycarbonyl)amino)-3-(4-(trifluoromethyl)phenyl)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: 89.0%

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile (58632-95-4) + (S)-4-trifluoromethylphenylalanine (3832-75-5,14091-16-8,114872-99-0,114926-38-4) → N-tert-butoxycarbonyl-L-4-trifluoromethylphenylalanine (82317-83-7,114873-07-3)

Guidance literature:

DOI:10.1248/cpb.37.826

Reference yield: 60.0%

4-bromomethyltrifluoromethylbenzene (402-49-3) → N-tert-butoxycarbonyl-L-4-trifluoromethylphenylalanine (82317-83-7,114873-07-3)

Guidance literature:

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + (S)-4-trifluoromethylphenylalanine (3832-75-5,14091-16-8,114872-99-0,114926-38-4) → N-tert-butoxycarbonyl-L-4-trifluoromethylphenylalanine (82317-83-7,114873-07-3)

Guidance literature:

With triethylamine; In water; acetone;

DOI:10.1021/jm00039a022

upstream raw materials:

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

(S)-4-trifluoromethylphenylalanine

di-tert-butyl dicarbonate

4-bromomethyltrifluoromethylbenzene

Refernces

• 1、 Hagiwara, Daijiro,Miyake, Hiroshi,Igari, Norihiro,Karino, Masako,Maeda, Yasue,et al.. "Studies of Neurokinin Antagonists. 4. Synthesis and Structure-Activity Relationships of Novel Dipeptide Substance P Antagonists: N2--L-prolyl>-N-methyl-N-(phenylmethyl)-3-(2-naphthyl)-L-alaninamide and Its Related Compounds". . p. 2090 - 2099. Retrieved 2007/10/02.