Boc-O-ethyl-L-tyrosine

Base Information

• Chemical Name: Boc-O-ethyl-L-tyrosine
• CAS No.: 76757-91-0
• Molecular Formula: C16H23NO5
• Molecular Weight: 309.362
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID90426917
• Nikkaji Number: J1.168.468H
• Wikidata: Q72449247
• Mol file: 76757-91-0.mol

Synonyms:Boc-O-ethyl-L-tyrosine;76757-91-0;Boc-Tyr(Et)-OH;(S)-2-((tert-Butoxycarbonyl)amino)-3-(4-ethoxyphenyl)propanoic acid;Boc-Tyr-OEt;(2S)-3-(4-ethoxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid;(2S)-2-{[(Tert-Butoxy)Carbonyl]Amino}-3-(4-Ethoxyphenyl)Propanoic Acid;SCHEMBL1000744;DTXSID90426917;NCLAAKQIHUIOIV-ZDUSSCGKSA-N;MFCD00065601;AKOS015836430;AKOS015890014;DS-2707;HY-W019683;N-tert-Butoxycarbonyl-O-ethyl-L-tyrosine;PD197040;CS-0030796;N-(tert-Butoxycarbonyl)-4-ethoxyphenylalanine;A838814;(S)-2-((tert-Butoxycarbonyl)amino)-3-(4-ethoxyphenyl)propanoicacid;(s)-2-(tert-butoxycarbonylamino)-3-(4-ethoxyphenyl)propanoic acid;(S)-2-tert-butoxycarbonylamino-3-(4-ethoxyphenyl)propionic acid;(2S)-3-(4-ethoxyphenyl)-2-[[(2-methylpropan-2-yl)oxy-oxomethyl]amino]propanoic acid

Chemical Property of Boc-O-ethyl-L-tyrosine

Chemical Property:

• Vapor Pressure: 9.7E-10mmHg at 25°C
• Refractive Index: 1.519
• Boiling Point: 472.7 °C at 760 mmHg
• Flash Point: 239.7 °C
• PSA: 84.86000
• Density: 1.149 g/cm³
• LogP: 2.99660
• Storage Temp.: Store at 0-5°C
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 309.15762283
• Heavy Atom Count: 22
• Complexity: 369

Purity/Quality:

99.9% ^*data from raw suppliers

Boc-O-ethyl-L-tyrosine 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC1=CC=C(C=C1)CC(C(=O)O)NC(=O)OC(C)(C)C
• Isomeric SMILES: CCOC1=CC=C(C=C1)C[C@@H](C(=O)O)NC(=O)OC(C)(C)C

Technology Process of Boc-O-ethyl-L-tyrosine

There total 8 articles about Boc-O-ethyl-L-tyrosine 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: 78.0%

diethyl sulfate (64-67-5) + Boc-Tyr-OH (3978-80-1) → N-tert-butoxycarbonyl-O-ethyl-L-tyrosine (76757-91-0,247088-44-4)

Guidance literature:

With sodium hydroxide; at 20 - 25 ℃;

Reference yield: 60.0%

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile (58632-95-4) + β-p-ethoxyphenyl-β-alanine (32795-52-1,3909-20-4,748068-32-8) → N-tert-butoxycarbonyl-O-ethyl-L-tyrosine (76757-91-0,247088-44-4)

Guidance literature:

DOI:10.1248/cpb.30.4435

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → N-tert-butoxycarbonyl-O-ethyl-L-tyrosine (76757-91-0,247088-44-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) K₂CO₃ / 1.) H₂O, 10 min, 2.) tert-butyl alcohol, ether, 25 min

2: K₂CO₃, 18-crown-6 / benzene / 1.5 h / Heating

3: NaOH / methanol; H₂O / 0.5 h

With sodium hydroxide; 18-crown-6 ether; potassium carbonate; In methanol; water; benzene;

DOI:10.1021/jo00322a049

upstream raw materials:

ethyl bromide

Boc-Tyr-OH

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

β-p-ethoxyphenyl-β-alanine

Downstream raw materials:

Boc-Tyr(Et)-Har-OMe

β-p-ethoxyphenyl-β-alanine

(2S)-3-tert-butoxycarbonylmaino-2-[[(2S)-2-tert-butoxycarbonylamino-3-(4-ethoxyphenyl)propionyl]-(4-phenoxybenzyl)amino]propionic acid methyl ester

O-ethyl-N-tert-butoxycarbonyl-L-tyrosine methyl ester

Refernces

• 1、 -. "Process to prepare (2S)-2-(dipropylamino)-6-ethoxy-2,3-dihydro-1H-indene-5-carboxamide". . . Retrieved 2008/06/13.
• 2、 Sasaki,Akutsu,Matsui,Suzuki,Sakurada,Sato,Kisara. "Studies on analgesic oligopeptides. II. Structure-activity relationship among thirty analogs of a cyclic dipeptide, cyclo(-Tyr-Arg-)". . p. 4435 - 4443. Retrieved 2007/10/02.