Boc-N-Me-Tyr-OH

Base Information

• Chemical Name: Boc-N-Me-Tyr-OH
• CAS No.: 82038-34-4
• Molecular Formula: C15H21NO5
• Molecular Weight: 295.335
• DSSTox Substance ID: DTXSID60427193
• Wikidata: Q72510310
• Mol file: 82038-34-4.mol

Synonyms:82038-34-4;Boc-N-Me-Tyr-OH;Boc-MeTyr-OH;N-Methyl-N-t-butoxycarbonyl-L-tyrosine;BOC-N-Methyl-L-tyrosine;(S)-2-((tert-butoxycarbonyl)(methyl)amino)-3-(4-hydroxyphenyl)propanoic acid;(2S)-3-(4-hydroxyphenyl)-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]propanoic acid;N-Boc-N-methyl-L-tyrosine;D-N-Boc-N-methyltyrosine;SCHEMBL6661008;DTXSID60427193;MFCD06658544;AKOS015850739;AM804375;DS-16134;CS-0154824;EN300-7405889;L-Tyrosine,N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-;(S)-2-(tert-butoxycarbonyl(methyl)amino)-3-(4-hydroxyphenyl)propanoic acid;(2S)-2-{[(tert-butoxy)carbonyl](methyl)amino}-3-(4-hydroxyphenyl)propanoic acid

Chemical Property of Boc-N-Me-Tyr-OH

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 1.52E-16mmHg at 25°C
• Melting Point: 140-142℃
• Boiling Point: 458.4 °C at 760 mmHg
• Flash Point: 231 °C
• PSA: 87.07000
• Density: 1.22 g/cm³
• LogP: 2.25480
• Storage Temp.: 2-8°C
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 295.14197277
• Heavy Atom Count: 21
• Complexity: 369

Purity/Quality:

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

N-Methyl-N-t-butoxycarbonyl-L-tyrosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N(C)C(CC1=CC=C(C=C1)O)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N(C)[C@@H](CC1=CC=C(C=C1)O)C(=O)O
• Uses: BOC-N-ME-TYR-OH is used in the preparation of tyrosyl derivatives as P2X7 receptor modulators.

Technology Process of Boc-N-Me-Tyr-OH

There total 10 articles about Boc-N-Me-Tyr-OH 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%

methyl N-(tert-butoxycarbonyl)-N-methyl-L-tyrosinate (112196-59-5) → (S)-2-((tert-butoxycarbonyl)(methyl)amino)-3-(4-hydroxyphenyl)propanoic acid (82038-34-4)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; water; at 25 ℃; for 1.2h;

DOI:10.1021/jo00238a005

Reference yield:

3-(4-benzyloxyphenyl)-(2R)-2-[(t-butoxycarbonyl)aminomethyl]propionate benzyl este → (S)-2-((tert-butoxycarbonyl)(methyl)amino)-3-(4-hydroxyphenyl)propanoic acid (82038-34-4)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; for 6h; under 1810.07 Torr;

Reference yield:

O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3,54784-43-9) → (S)-2-((tert-butoxycarbonyl)(methyl)amino)-3-(4-hydroxyphenyl)propanoic acid (82038-34-4)

Guidance literature:

Multi-step reaction with 2 steps

1: NaH / tetrahydrofuran; dimethylformamide / 10 h / 0 - 25 °C

2: H₂ / Pd-C / methanol / 25 °C

With hydrogen; sodium hydride; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1021/jo9604144

upstream raw materials:

methyl N-(tert-butoxycarbonyl)-N-methyl-L-tyrosinate

O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

L-Tyr-OMe

(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Downstream raw materials:

1-[(S)-N-tert-butyloxycarbonyl-N-methyltyrosyl]-4-(4-nitrophenyl)piperazine

C₄₆H₅₁F₅N₆O₁₀*C₂HF₃O₂

H-N-Me-Tyr-N-Me-Tyr-OMe

Boc-D-Ala-Ala-N-Me-Tyr(OMe)-Ala-N-Me-Tyr-N-Me-Tyr-OH

Refernces

• 1、 Karmakar, Ananta,Basha, Mushkin,Venkatesh Babu,Botlagunta, Murali,Malik, Noormohamed Abdul,Rampulla, Richard,Mathur, Arvind,Gupta, Arun Kumar. "Tertiary-butoxycarbonyl (Boc) – A strategic group for N-protection/deprotection in the synthesis of various natural/unnatural N-unprotected aminoacid cyanomethyl esters". . p. 4267 - 4271. Retrieved 2018/11/03.
• 2、 Boger, Dale L.,Zhou, Jiacheng. "Alternative synthesis of the cycloisodityrosine subunit of deoxybouvardin, RA-VII, and related agents: Reassignment of the stereochemistry of prior intermediates". . p. 3938 - 3939. Retrieved 2007/10/03.