CID 11068914

Base Information

• Chemical Name: CID 11068914
• CAS No.: 16652-76-9
• Molecular Formula: C12H17NO2^.C7H8O3S
• Molecular Weight: 379.477
• Hs Code.: 2922499990
• Mol file: 16652-76-9.mol

Synonyms:SCHEMBL12098466

Chemical Property of CID 11068914

Chemical Property:

• Appearance/Colour: Crystalline
• Vapor Pressure: 0.0028mmHg at 25°C
• Melting Point: 160-162 °C
• Boiling Point: 285.5 °C at 760 mmHg
• Flash Point: 143.7 °C
• PSA: 115.07000
• LogP: 4.73590
• Storage Temp.: −20°C
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 379.14534407
• Heavy Atom Count: 26
• Complexity: 391

Purity/Quality:

99% ^*data from raw suppliers

L-Valine benzyl ester 4-toluenesulfonate salt ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)[O-].CC(C)C(C(=O)OCC1=CC=CC=C1)[NH3+]
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)[O-].CC(C)[C@@H](C(=O)OCC1=CC=CC=C1)[NH3+]
• Uses: Val-OBzl TosOH is a L-Valine derivative useful as intermediate for the preparation of peptides.

Technology Process of CID 11068914

There total 7 articles about CID 11068914 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: 99.0%

toluene-4-sulfonic acid (104-15-4) + (S)-2-(Benzhydrylidene-amino)-3-methyl-butyric acid benzyl ester (138892-14-5) → L-valine benzyl ester p-toluenesulfonate salt (16652-76-9)

Guidance literature:

In water; acetonitrile; Ambient temperature;

DOI:10.1055/s-1991-26625

Reference yield: 91.0%

L-valine (72-18-4,25609-85-2,7004-03-7,921-10-8) + toluene-4-sulfonic acid (104-15-4) + benzyl alcohol (100-51-6,185532-71-2) → L-valine benzyl ester p-toluenesulfonate salt (16652-76-9)

Guidance literature:

In toluene; for 5h; Reflux;

DOI:10.1016/j.tetlet.2008.09.027

Reference yield:

L-Valine methyl ester (4070-48-8) → L-valine benzyl ester p-toluenesulfonate salt (16652-76-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent

2: 1) 20percent aq.NaOH, Bu₄NHSO₄ / 1) MeCN, r.t., 16 h, 2) CH₂Cl₂, r.t., 6 h

3: 99 percent / acetonitrile; H₂O / Ambient temperature

With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; In water; acetonitrile;

DOI:10.1055/s-1991-26625

upstream raw materials:

toluene-4-sulfonic acid

(S)-2-(Benzhydrylidene-amino)-3-methyl-butyric acid benzyl ester

L-valine

benzyl alcohol

Downstream raw materials:

N-Formyl-L-valine benzyl ester

L-Valyl-L-valine benzyl ester

Bn-L-Val-(diketo-L-Asp)-L-Val-Bn

(S)-benzyl 2-((S)-2-((tert-butoxycarbonyl)amino)-3-methylbutanamido)-3-methylbutanoate

Refernces

• 1、 Bolchi, Cristiano,Bavo, Francesco,Pallavicini, Marco. "One-step preparation of enantiopure l- or d-amino acid benzyl esters avoiding the use of banned solvents". . p. 965 - 974. Retrieved 2017/04/11.
• 2、 Biondini, Daniele,Brinchi, Lucia,Germani, Raimondo,Goracci, Laura,Savelli, Gianfranco. "Esterification of unprotected a-Amino acids in ionic liquids as the reaction media". experimental part. p. 39 - 44. Retrieved 2010/08/22.