3-(4-Bromophenyl)-2-{[tert-butoxy(hydroxy)methylidene]amino}propanoate

Base Information

• Chemical Name: 3-(4-Bromophenyl)-2-{[tert-butoxy(hydroxy)methylidene]amino}propanoate
• CAS No.: 62129-39-9
• Molecular Formula: C14H18BrNO4
• Molecular Weight: 344.205
• Hs Code.: 29223900
• DSSTox Substance ID: DTXSID70977730
• Wikidata: Q72448753
• Mol file: 62129-39-9.mol

Synonyms:DTXSID70977730;3-(4-Bromophenyl)-2-{[tert-butoxy(hydroxy)methylidene]amino}propanoate

Chemical Property of 3-(4-Bromophenyl)-2-{[tert-butoxy(hydroxy)methylidene]amino}propanoate

Chemical Property:

• Appearance/Colour: off-white powder
• Vapor Pressure: 7.71E-10mmHg at 25°C
• Melting Point: 118 °C
• Refractive Index: 1.551
• Boiling Point: 475.3 °C at 760 mmHg
• PKA: 3.83±0.10(Predicted)
• Flash Point: 241.2 °C
• PSA: 75.63000
• Density: 1.405 g/cm³
• LogP: 3.36040
• Storage Temp.: Store at RT.
• Water Solubility.: Slightly soluble in water.
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 342.03410
• Heavy Atom Count: 20
• Complexity: 340

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC=C(C=C1)Br)C(=O)[O-]
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC1=CC=C(C=C1)Br)C(=O)[O-]
• Uses: N-Boc-4-bromo-L-phenylalanine is used as pharmaceutical intermediate.

Technology Process of 3-(4-Bromophenyl)-2-{[tert-butoxy(hydroxy)methylidene]amino}propanoate

There total 5 articles about 3-(4-Bromophenyl)-2-{[tert-butoxy(hydroxy)methylidene]amino}propanoate 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: 96.9%

di-tert-butyl dicarbonate (24424-99-5) + H-p-BrPhe-OH (24250-84-8) → 4-bromo-N-{[(1,1-dimethylethyl)oxy]carbonyl}-L-phenylalanine (62129-39-9,79561-82-3)

Guidance literature:

With potassium carbonate; In methanol; water; at 20 ℃;

Reference yield: 33.0%

N-(tert-butoxycarbonyl)-1-(4-bromophenyl)-1-(2-furyl)ethylamine → 4-bromo-N-{[(1,1-dimethylethyl)oxy]carbonyl}-L-phenylalanine (62129-39-9,79561-82-3)

Guidance literature:

With ruthenium trichloride; sodium periodate; In tetrachloromethane; acetonitrile; for 0.333333h;

DOI:10.1039/b310624a

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + 3-(4-bromophenyl)acrylic acid (1200-07-3) → tert-butyl carbazate (4248-19-5) + 4-bromo-N-{[(1,1-dimethylethyl)oxy]carbonyl}-L-phenylalanine (62129-39-9,79561-82-3)

Guidance literature:

3-(4-bromophenyl)acrylic acid; With ammonium hydroxide; at 37 ℃; for 18h; pH=9.6; Enzymatic reaction;

di-tert-butyl dicarbonate;

DOI:10.1021/acscatal.5b01132

upstream raw materials:

di-tert-butyl dicarbonate

H-p-BrPhe-OH

3-(4-bromophenyl)acrylic acid

(S)-2-amino-3-(4-bromophenyl)propanoic acid hydrochloride

Downstream raw materials:

[2-(4-bromo-phenyl)-1-(methoxy-methyl-carbamoyl)-ethyl]-carbamic acid tert-butyl ester

(S)-3-Amino-4-(4-bromo-phenyl)-butyric acid

(S)-methyl 4-(4-bromophenyl)-3-{[(tert-butoxy)carbonyl]amino}butanoate

(S)-3-{[(tert-butoxy)carbonyl]amino}-4-(4-bromophenyl)-1-diazobutan-2-one

Refernces

• 1、 Aggarwal, Anupriya,Ashhurst, Anneliese S.,Bedding, Max J.,Beretta, Laura,Drelich, Aleksandra,Gerwick, William H.,Hook, Vivian,Larance, Mark,Li, Linfeng,McKerrow, James H.,Meek, Thomas D.,O'Donoghue, Anthony J.,Payne, Richard J.,Pwee, Dustin,Skinner, Danielle,Stoye, Alexander,Tang, Arthur H.,Tseng, Chien-Te,Turville, Stuart,Yoon, Michael C.,Fajtová, Pavla. "Potent Anti-SARS-CoV-2 Activity by the Natural Product Gallinamide A and Analogues via Inhibition of Cathepsin L". supporting information. . Retrieved 2021/11/18.
• 2、 Ahmed, Syed T.,Parmeggiani, Fabio,Weise, Nicholas J.,Flitsch, Sabine L.,Turner, Nicholas J.. "Chemoenzymatic Synthesis of Optically Pure l- and d-Biarylalanines through Biocatalytic Asymmetric Amination and Palladium-Catalyzed Arylation". . p. 5410 - 5413. Retrieved 2015/09/15.