2-(2-{[(Benzyloxy)carbonyl]amino}-3-methylbutanamido)acetic acid

Base Information

• Chemical Name: 2-(2-{[(Benzyloxy)carbonyl]amino}-3-methylbutanamido)acetic acid
• CAS No.: 2790-84-3
• Molecular Formula: C₁₅H₂₀N₂O₅
• Molecular Weight: 308.334
• DSSTox Substance ID: DTXSID30384380
• Mol file: 2790-84-3.mol

Synonyms:Z-L-valyl-L-glycine;2-[[3-methyl-2-(phenylmethoxycarbonylamino)butanoyl]amino]acetic acid;SCHEMBL2119163;CARBOBENZYLOXYVALYLGLYCINE;DTXSID30384380;2-(2-{[(benzyloxy)carbonyl]amino}-3-methylbutanamido)acetic acid;AKOS030241223;CCG-242567;FT-0634490;J-016914

Chemical Property of 2-(2-{[(Benzyloxy)carbonyl]amino}-3-methylbutanamido)acetic acid

Chemical Property:

• Vapor Pressure: 3.73E-14mmHg at 25°C
• Melting Point: 121 - 123 °C (hexane)
• Boiling Point: 577°C at 760 mmHg
• Flash Point: 302.8°C
• PSA: 104.73000
• Density: 1.226g/cm³
• LogP: 1.92000
• Storage Temp.: -15°C
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 308.13722174
• Heavy Atom Count: 22
• Complexity: 391

Purity/Quality:

99% ^*data from raw suppliers

Z-L-valyl-L-glycine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C(=O)NCC(=O)O)NC(=O)OCC1=CC=CC=C1

Technology Process of 2-(2-{[(Benzyloxy)carbonyl]amino}-3-methylbutanamido)acetic acid

There total 19 articles about 2-(2-{[(Benzyloxy)carbonyl]amino}-3-methylbutanamido)acetic acid 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: 92.0%

N,O-bis(trimethylsilyl)glycine (7364-42-3) + (S)-N-(benzyloxycarbonyl)valine (1149-26-4) → N-(N-benzyloxycarbonyl-L-valyl)-glycine (22221-75-6,74088-26-9,2790-84-3)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 ℃; Inert atmosphere;

DOI:10.1021/jo2024703

Reference yield: 88.0%

2-Benzyloxycarbonylamino-3-methyl-butyric acid 4-nitro-phenyl ester (3411-74-3,4108-18-3,10512-93-3,10512-94-4) + glycine (56-40-6,18875-39-3,25718-94-9) → N-(N-benzyloxycarbonyl-L-valyl)-glycine (22221-75-6,74088-26-9,2790-84-3)

Guidance literature:

In sodium hydroxide;

DOI:10.1007/BF00597661

Reference yield: 80.0%

N-benzyloxycarbonyl-L-valine pentafluorophenyl ester (25529-25-3) + glycine (56-40-6,18875-39-3,25718-94-9) → N-(N-benzyloxycarbonyl-L-valyl)-glycine (22221-75-6,74088-26-9,2790-84-3)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; for 0.00833333h; microwave irradiation;

upstream raw materials:

ethyl N-(benzyloxycarbonyl)-L-valylglycinate

N-benzyloxycarbonylvalylglycine methyl ester

(S)-N-(benzyloxycarbonyl)valine

glycine

Downstream raw materials:

valylglycine

Benzyloxycarbonylval-gly-tert.-butyloxycarbonylhydrazin

(S)-tert-butyl 2-(2-(((benzyloxy)carbonyl)amino)-3-methylbutanamido)acetate

[(S)-2-((S)-2-Benzyloxycarbonylamino-propionylamino)-3-methyl-butyrylamino]-acetic acid

Refernces

• 1、 Singh, Palwinder,Kaur, Sukhmeet,Kaur, Jagroop,Singh, Gurjit,Bhatti, Rajbir. "Rational Design of Small Peptides for Optimal Inhibition of Cyclooxygenase-2: Development of a Highly Effective Anti-Inflammatory Agent". supporting information. p. 3920 - 3934. Retrieved 2016/05/24.
• 2、 Singh, Palwinder,Singh, Amrinder,Kaur, Sukhmeet,Mithu, Venus Singh,Bhatti, Manpreet S.. "Temperature, pH and H-bond synergism for peptide bond formation: Synthesis of sequence specific tetra- and penta-peptides without using coupling reagent". . p. 37371 - 37374. Retrieved 2014/12/11.