(S)-N-Boc-3-Bromophenylalanine

Base Information

• Chemical Name: (S)-N-Boc-3-Bromophenylalanine
• CAS No.: 82278-73-7
• Molecular Formula: C14H18BrNO4
• Molecular Weight: 344.205
• Hs Code.: 2924299090
• UNII: VYL82Z3H4B
• DSSTox Substance ID: DTXSID90370325
• Wikidata: Q72448742
• Mol file: 82278-73-7.mol

Synonyms:82278-73-7;(S)-N-Boc-3-Bromophenylalanine;Boc-3-bromo-L-phenylalanine;BOC-PHE(3-BR)-OH;Boc-L-3-Bromophenylalanine;(S)-3-(3-Bromophenyl)-2-((tert-butoxycarbonyl)amino)propanoic acid;N-BOC-3-BROMO-L-PHENYLALANINE;(2S)-3-(3-bromophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid;(S)-3-(3-bromophenyl)-2-(tert-butoxycarbonylamino)propanoic acid;(2S)-3-(3-BROMOPHENYL)-2-(TERT-BUTOXYCARBONYLAMINO)PROPIONIC ACID;BOC-L-3-BROMOPHE;(2S)-3-(3-bromophenyl)-2-{[(tert-butoxy)carbonyl]amino}propanoic acid;(S)-N-Alpha-T-Butyloxycarbonyl-3-Bromo-Phenylalanine;BOC-L-3-BR-PHE-OH;(S)-3-(3-Bromophenyl)-2-[(tert-butoxycarbonyl)amino]propanoic acid;MFCD01317710;(2S)-3-(3-bromophenyl)-2-[(tert-butoxycarbonyl)amino]propanoic acid;VYL82Z3H4B;SCHEMBL1073538;DTXSID90370325;FBUDYESOPLBQIR-NSHDSACASA-N;BCP06282;(2S)-2-[(tert-butoxy)carbonylamino]-3-(3-bromophenyl)propanoic acid;ZB0894;AKOS015889863;AKOS015969354;AC-4516;AM82711;CS-W022606;GS-2601;HY-W041866;N-tert-Butoxycarbonyl-L-3-Bromo Phenylalanine;A50143;EN300-3414681;A840290;Q-101731;3-Bromo-N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanine;L-Phenylalanine, 3-bromo-N-[(1,1-dimethylethoxy)carbonyl]-;(S)-2-(tert-Butoxycarbonylamino)-3-(3-bromophenyl)propanoic acid;(S)-3-(3-Bromophenyl)-2-[(tert-butoxycarbonyl)amino]propionic acid

Chemical Property of (S)-N-Boc-3-Bromophenylalanine

Chemical Property:

• Appearance/Colour: off-white powder
• Vapor Pressure: 7.71E-10mmHg at 25°C
• Melting Point: 106.1oC
• Refractive Index: 1.6500 (estimate)
• Boiling Point: 475.3 °C at 760 mmHg
• PKA: 3.81±0.10(Predicted)
• Flash Point: 241.2 °C
• PSA: 75.63000
• Density: 1.405 g/cm³
• LogP: 3.36040
• Storage Temp.: Store at 0°C
• Water Solubility.: Slightly soluble in water.
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 343.04192
• Heavy Atom Count: 20
• Complexity: 354

Purity/Quality:

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

(S)-N-Boc-3-Bromophenylalanine ^*data from reagent suppliers

Safty Information:

• Safety Statements: S24/25:Avoid contact with skin and eyes.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC(=CC=C1)Br)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC1=CC(=CC=C1)Br)C(=O)O
• Uses: N-Boc-3-bromo-L-phenylalanine is used as pharmaceutical intermediate.

Technology Process of (S)-N-Boc-3-Bromophenylalanine

There total 3 articles about (S)-N-Boc-3-Bromophenylalanine 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: 98.0%

di-tert-butyl dicarbonate (24424-99-5) + (S)-2-amino-3-(3-bromophenyl)propanoic acid (82311-69-1,99295-78-0) → (2S)-3-(3-bromophenyl)-2-[(tert-butoxycarbonyl)amino]propanoic acid (82278-73-7)

Guidance literature:

With sodium hydrogencarbonate; In 1,4-dioxane; water; at 20 ℃;

DOI:10.1021/ml2002482

Reference yield: 17.0%

2-amino-3-(3-bromo-phenyl)-N-((2R)-hydroxy-(1R)-methyl-2-phenyl-ethyl)-N-methyl-propionamide (880347-42-2) + di-tert-butyl dicarbonate (24424-99-5) → (2S)-3-(3-bromophenyl)-2-[(tert-butoxycarbonyl)amino]propanoic acid (82278-73-7)

Guidance literature:

2-amino-3-(3-bromo-phenyl)-N-((2R)-hydroxy-(1R)-methyl-2-phenyl-ethyl)-N-methyl-propionamide; With sodium hydroxide; In water; for 2h; Heating / reflux;

di-tert-butyl dicarbonate; With sodium hydrogencarbonate; In 1,4-dioxane; at 0 - 20 ℃;

Reference yield:

3-bromocinnamic acid (14473-91-7,20595-41-9,32862-97-8) → (2S)-3-(3-bromophenyl)-2-[(tert-butoxycarbonyl)amino]propanoic acid (82278-73-7)

Guidance literature:

Multi-step reaction with 2 steps

1: recombinant cyanobacterium Anabaena variabilis phenylalanine ammonia lyase; ammonium carbamate / water / 24 h / 30 °C / Enzymatic reaction

2: caesium carbonate / water; tetrahydrofuran / 0.33 h / 90 °C / Microwave irradiation

With recombinant cyanobacterium Anabaena variabilis phenylalanine ammonia lyase; ammonium carbamate; caesium carbonate; In tetrahydrofuran; water;

DOI:10.1039/c6cy00855k

upstream raw materials:

di-tert-butyl dicarbonate

(S)-2-amino-3-(3-bromophenyl)propanoic acid

2-amino-3-(3-bromo-phenyl)-N-((2R)-hydroxy-(1R)-methyl-2-phenyl-ethyl)-N-methyl-propionamide

3-bromocinnamic acid

Downstream raw materials:

(S)-3-Biphenyl-3-yl-2-tert-butoxycarbonylamino-propionic acid

methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate

Refernces

• 1、 Weise, Nicholas J.,Ahmed, Syed T.,Parmeggiani, Fabio,Siirola, Elina,Pushpanath, Ahir,Schell, Ursula,Turner, Nicholas J.. "Intensified biocatalytic production of enantiomerically pure halophenylalanines from acrylic acids using ammonium carbamate as the ammonia source". . p. 4086 - 4089. Retrieved 2016/07/06.
• 2、 Zhong, Min,Gadek, Thomas R.,Bui, Minna,Shen, Wang,Burnier, John,Barr, Kenneth J.,Hanan, Emily J.,Oslob, Johan D.,Yu, Chul H.,Zhu, Jiang,Arkin, Michelle R.,Evanchik, Marc J.,Flanagan, W. Mike,Hoch, Ute,Hyde, Jennifer,Prabhu, Saileta,Silverman, Jeffrey A.,Wright, Jasmin. "Discovery and development of potent LFA-1/ICAM-1 antagonist SAR 1118 as an ophthalmic solution for treating dry eye". supporting information; scheme or table. p. 203 - 206. Retrieved 2012/05/04.