N-(tert-Butoxycarbonyl)-L-phenylalanine

Base Information

• Chemical Name: N-(tert-Butoxycarbonyl)-L-phenylalanine
• CAS No.: 13734-34-4
• Deprecated CAS: 92761-90-5
• Molecular Formula: C14H19NO4
• Molecular Weight: 265.309
• Hs Code.: 29242990
• European Community (EC) Number: 237-305-5
• DSSTox Substance ID: DTXSID90884634
• Nikkaji Number: J124.089G
• Wikidata: Q72510378
• ChEMBL ID: CHEMBL1222330
• Mol file: 13734-34-4.mol

Synonyms:Alanine,N-carboxy-3-phenyl-, N-tert-butyl ester, L- (8CI);(S)-2-(tert-Butoxycarbonylamino)-3-phenylpropanoic acid;(S)-N-(tert-Butoxycarbonyl)phenylalanine;BOC-L-Phenylalanine;N-(tert-Butoxycarbonyl)-(S)-phenylalanine;N-(tert-Butyloxycarbonyl)phenylalanine;N-BOC-L-phenylalanine;N-[(1,1-Dimethylethoxy)carbonyl]-L-phenylalanine;NSC111172;Boc-Phe-OH;BOC-L-Phe-OH;

Chemical Property of N-(tert-Butoxycarbonyl)-L-phenylalanine

Chemical Property:

• Appearance/Colour: white fine crystalline powder
• Vapor Pressure: 4.88E-08mmHg at 25°C
• Melting Point: 85-87 °C(lit.)
• Refractive Index: 24.5 ° (C=1, EtOH)
• Boiling Point: 426.6 °C at 760 mmHg
• PKA: 3.88±0.10(Predicted)
• Flash Point: 211.8 °C
• PSA: 75.63000
• Density: 1.16 g/cm³
• LogP: 2.59790
• Storage Temp.: -20°C
• Solubility.: Soluble in methanol, dichloromethane, dimethylformamide and N-me
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 265.13140809
• Heavy Atom Count: 19
• Complexity: 316

Purity/Quality:

99% ^*data from raw suppliers

N-Boc-L-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 36-22-36/37/38-20/21/22
• Safety Statements: 39-26-36-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC=CC=C1)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O
• Uses: N-(tert-Butoxycarbonyl)-L-phenylalanine is used in enantioselective hydrolysis of amino acid esters. Acts as an inhibitor of gastric acid secretion. N-Boc-L-phenylalanine is a derivative of Phenylalanine used in enantioselective hydrolysis of amino acid esters.

Technology Process of N-(tert-Butoxycarbonyl)-L-phenylalanine

There total 142 articles about N-(tert-Butoxycarbonyl)-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: 100.0%

2-tert-butoxycarbonylamino-3-phenylpropionic acid allyl ester (160788-63-6) → N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4)

Guidance literature:

With pyrrolidine; resin-plug bound Pd; In tetrahydrofuran; for 24h; Heating;

DOI:10.1016/S0040-4039(03)00977-8

Reference yield: 99.0%

(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester (51987-73-6) → N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4)

Guidance literature:

(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester; With dimethylsulfoxonium methylide; In tetrahydrofuran; at 20 ℃; for 0.333333h; Inert atmosphere;

With potassium hydrogensulfate; water; In ethyl acetate; pH=3; Inert atmosphere;

DOI:10.1002/ejoc.201101031

Reference yield: 99.0%

C20H31NO4S2 → N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; 2-hydroxyethanethiol; at 20 - 25 ℃; for 0.166667h; Reagent/catalyst; Time;

DOI:10.1021/acs.orglett.8b02459

upstream raw materials:

N-(tert-butyloxycarbonyl) azide

L-phenylalanine

tert-Butyl 4-nitrophenyl carbonate

(L)-phenylalanine ethyl ester hydrochloride

Downstream raw materials:

ethyl (N-tert-butoxycarbonyl-L-phenylalanyl)glycinate

N-(N-(1,1-dimethylethoxycarbonyl)-L-phenylalanyl)-L-valine methyl ester

{(S)-1-[((S)-1-Carbamoyl-3-methyl-butyl)-methyl-carbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester

{(S)-1-[((R)-1-Carbamoyl-2-ethylsulfanyl-ethyl)-methyl-carbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester

Refernces

• 1、 Moitra, Parikshit,Kumar, Krishan,Kondaiah, Paturu,Bhattacharya, Santanu. "Efficacious anticancer drug delivery mediated by a pH-sensitive self-assembly of a conserved tripeptide derived from tyrosine kinase NGF receptor". . p. 1113 - 1117. Retrieved 2014.
• 2、 Mohanrao, Raja,Sureshan, Kana M.. "Synthesis and Reversible Hydration of a Pseudoprotein, a Fully Organic Polymeric Desiccant by Multiple Single-Crystal-to-Single-Crystal Transformations". . p. 12435 - 12439. Retrieved 2018.
• 3、 Kusebauch, Ulrike,Beck, Barbara,Messer, Kim,Herdtweck, Eberhardt,Doemling, Alexander. "Massive Parallel Catalyst Screening: Toward Asymmetric MCRs". . p. 4021 - 4024. Retrieved 2003.
• 4、 -. "Chiral secondary phosphine oxide pre-ligand and application thereof". Paragraph 0040-0043. . Retrieved 2021/10/20.
• 5、 -. "CONJUGATE OF FLUORESCENT DYE FOR THE VISUALIZATION OF PSMA EXPRESSING CELLS". Page/Page column 10; 15. . Retrieved 2021/01/23.