Boc-4-chloro-L-phenylalanine

Base Information

• Chemical Name: Boc-4-chloro-L-phenylalanine
• CAS No.: 68090-88-0
• Molecular Formula: C₁₄H₁₈ClNO₄
• Molecular Weight: 299.754
• Hs Code.: 29242990
• DSSTox Substance ID: DTXSID80370339
• Nikkaji Number: J719.349A
• Mol file: 68090-88-0.mol

Synonyms:68090-88-0;Boc-Phe(4-Cl)-OH;Boc-L-4-Chlorophenylalanine;Boc-4-chloro-L-phenylalanine;N-Boc-4-chloro-L-phenylalanine;Boc-L-phe(4-Cl)-OH;N-(tert-Butoxycarbonyl)-4-chloro-L-phenylalanine;(2S)-3-(4-chlorophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid;Boc-L-4-Chlorophe;L-PHENYLALANINE, 4-CHLORO-N-[(1,1-DIMETHYLETHOXY)CARBONYL]-;(S)-2-(tert-butoxycarbonylamino)-3-(4-chlorophenyl)propanoic acid;boc-p-fluoro-phe-oh;(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(4-chlorophenyl)propanoic acid;(S)-2-((tert-Butoxycarbonyl)amino)-3-(4-chlorophenyl)propanoic acid;(S)-N-BOC-4-Chlorophenylalanine;BOC-P-CHLORO-PHE-OH;BOC-4-CHLORO-PHE-OH;BOC-4-CHLORO-PHENYLALANINE;MFCD00057808;N-(tert-Butoxycarbonyl)-4-chlorophenylalanine;Boc-Phe-(4-Cl)-OH;Boc-4-chloro L-phenylalanine;SCHEMBL181848;(S)-2-(Boc-amino)-3-(4-chloro-phenyl)-propionic acid;Boc-4-chloro-Phe-OH;DTXSID80370339;BETBOAZCLSJOBQ-NSHDSACASA-N;(S)-N-Boc-4-chlorophenyl alanine;BOC-P-CHLORO-L-PHENYLALANINE;Nalpha -Boc-(p-chloro) phenylalanine;AKOS015836557;AKOS015889982;AC-9881;CS-W008486;GS-0030;HY-W008486;SS-6058;AM804225;B3614;Boc-Phe(4-Cl)-OH, >=96.0% (TLC);M03181;W10601;EN300-3367018;Boc-L-4-chlorophenylalanine (Boc-L-Phe(4-Cl)-OH);J-300389;(S)-3-(4-chlorophenyl)-2-(tert-butoxycarbonylamino)propanoic acid;2(s)-tert-butoxycarbonylamino-3-(4-chlorophenyl)-propionic acid

Chemical Property of Boc-4-chloro-L-phenylalanine

Chemical Property:

• Appearance/Colour: pale yellow granular powder
• Melting Point: 108 °C
• Refractive Index: 1.6800 (estimate)
• Boiling Point: 452.5 °C at 760 mmHg
• PKA: 3.83±0.10(Predicted)
• Flash Point: 227.5 °C
• PSA: 75.63000
• Density: 1.245 g/cm³
• LogP: 3.25130
• Storage Temp.: Store at RT.
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 299.0924357
• Heavy Atom Count: 20
• Complexity: 346

Purity/Quality:

99% ^*data from raw suppliers

Boc-4-chloro-L-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC=C(C=C1)Cl)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC1=CC=C(C=C1)Cl)C(=O)O
• Uses: BOC-4-chlorophenylalanine, is an amino acid building block used in peptide synthesis. With a growing peptide drug market the fast, reliable synthesis of peptides is of great importance.

Technology Process of Boc-4-chloro-L-phenylalanine

There total 17 articles about Boc-4-chloro-L-phenylalanine 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: 95.0%

di-tert-butyl dicarbonate (24424-99-5) + DL-Phe(4Cl) (7424-00-2,1991-78-2) → 2-(R)-tert-butoxycarbonylamino-3-(4-chloro-phenyl)-propionic acid (57292-44-1,68090-88-0,129101-26-4,51301-86-1)

Guidance literature:

With sodium carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; water; 1.) 0 deg C, 30 min; 2.) up to RT, 1h;

Reference yield: 91.0%

(4S,2S)-4-Chloro-<2-<<(1,1-dimethylethoxy)carbonyl>amino>-3-oxo-3-<2-oxo-4-(phenylmethyl)-3-oxazolidinyl>propyl>benzene (159750-06-8) → Boc-p-chloro-L-Phe-OH (51301-86-1,57292-44-1,129101-26-4,68090-88-0)

Guidance literature:

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; for 1h;

DOI:10.1021/jo970508t

Reference yield: 81.6%

di-tert-butyl dicarbonate (24424-99-5) + p-chlorophenylalanine (14173-39-8,1991-78-2) → Boc-p-chloro-L-Phe-OH (51301-86-1,57292-44-1,129101-26-4,68090-88-0)

Guidance literature:

With aqueous 27percent NaOH; In methanol; water; at 30 ℃; for 4h;

upstream raw materials:

di-tert-butyl dicarbonate

DL-Phe(4Cl)

N-(tert-butyloxycarbonyl) azide

p-chlorophenylalanine

Downstream raw materials:

N-<(1,1-Dimethylethoxy)carbonyl>-4-chloro-L-phenylalanine 2-bromoethyl ester

[[2-tert-butoxycarbonylamino-3-(4-chloro-phenyl)-propionyl]-(3-phenyl-propyl)-amino]-acetic acid methyl ester

C₂₉H₄₁ClN₄O₃

C₂₄H₃₉ClN₄O₃

Refernces

• 1、 Koralewski, Robert,Dymek, Barbara,Mazur, Marzena,Sklepkiewicz, Piotr,Olejniczak, Sylwia,Czestkowski, Wojciech,Matyszewski, Krzysztof,Andryianau, Gleb,Niedziejko, Piotr,Kowalski, Michal,Gruza, Mariusz,Borek, Bart?omiej,Jedrzejczak, Karol,Bartoszewicz, Agnieszka,Pluta, El?bieta,Rymaszewska, Aleksandra,Kania, Magdalena,Rejczak, Tomasz,Piasecka, Sylwia,Mlacki, Michal,Mazurkiewicz, Marcin,Piotrowicz, Micha?,Salamon, Magdalena,Zagozdzon, Agnieszka,Napiorkowska-Gromadzka, Agnieszka,Bartlomiejczak, Aneta,Mozga, Witold,Dobrzański, Pawe?,Dzwonek, Karolina,Golab, Jakub,Nowotny, Marcin,Olczak, Jacek,Golebiowski, Adam. "Discovery of OATD-01, a First-in-Class Chitinase Inhibitor as Potential New Therapeutics for Idiopathic Pulmonary Fibrosis". supporting information. p. 15527 - 15540. Retrieved 2020/11/17.
• 2、 -. "SUBSTITUTED AMINO TRIAZOLES USEFUL AS HUMAN CHITINASE INHIBITORS". Page/Page column 138; 139. . Retrieved 2017/03/21.