Boc-Val-chloromethylketone

Base Information

• Chemical Name: Boc-Val-chloromethylketone
• CAS No.: 103542-47-8
• Molecular Formula: C₁₁H₂₀ClNO₃
• Molecular Weight: 249.738
• Hs Code.: 2924199090
• DSSTox Substance ID: DTXSID50552488
• Nikkaji Number: J835.959H
• Wikidata: Q82432775
• Mol file: 103542-47-8.mol

Synonyms:Boc-Val-chloromethylketone;103542-47-8;Boc-L-Valine chloromethyl ketone;TERT-BUTYL N-[(3S)-1-CHLORO-4-METHYL-2-OXOPENTAN-3-YL]CARBAMATE;Boc-ValCH2Cl;(S)-tert-Butyl (1-chloro-4-methyl-2-oxopentan-3-yl)carbamate;DTXSID50552488;HQCFUDZWXVYJEF-VIFPVBQESA-N;MFCD11113165;BS-26049;A1867;CS-0210571;G39043;(4-Chloro-3-methyl-1H-pyrazol-1-yl)aceticacid;EN300-7192517;(3S)-3-(Boc-amino)-1-chloro-4-methyl-2-oxopentane;(S)-tert-butyl 1-chloro-4-methyl-2-oxopentan-3-ylcarbamate;tert-Butyl [(3S)-1-chloro-4-methyl-2-oxopentan-3-yl]carbamate;Carbamic acid,[3-chloro-1-(1-methylethyl)-2-oxopropyl]-,1,1-dimethylethyl ester,(S)-(9ci)

Chemical Property of Boc-Val-chloromethylketone

Chemical Property:

• Melting Point: 68-69 °C
• Boiling Point: 334.3±22.0 °C(Predicted)
• PKA: 10.90±0.46(Predicted)
• PSA: 58.89000
• Density: 1.077±0.06 g/cm3(Predicted)
• LogP: 2.54800
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 249.1131712
• Heavy Atom Count: 16
• Complexity: 258

Purity/Quality:

99% ^*data from raw suppliers

Boc-Val-Chloromethylketone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Boc-Val-chloromethylketone

There total 4 articles about Boc-Val-chloromethylketone 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: 50.0%

Chloroiodomethane (593-71-5) + N-tert-butoxycarbonyl-L-valine methyl ester (58561-04-9) → Boc-Val-CH2Cl (103542-47-8)

Guidance literature:

With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -75 ℃; for 0.166667h;

DOI:10.1016/S0040-4039(97)00605-9

Reference yield:

Chloroiodomethane (593-71-5) + N-tertbutyloxycarbonyl-S-valine methyl ester (110694-59-2) → Boc-Val-CH2Cl (103542-47-8)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -90 ℃;

DOI:10.1016/S0960-894X(02)00840-5

Reference yield:

t-Boc-L-valine (13734-41-3) → Boc-Val-CH2Cl (103542-47-8)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine

2: 2.) 8.4 N HCl / 1.) THF, 4 deg C, 15 h, 2.) THF, dioxane, -15 deg C, 3 h

With hydrogenchloride; triethylamine;

DOI:10.1248/cpb.35.3576

upstream raw materials:

diazomethane

C₁₃H₂₃NO₅

Chloroiodomethane

N-tert-butoxycarbonyl-L-valine methyl ester

Downstream raw materials:

tert-butyl (S)-2-methyl-1-((S)-oxiran-2-yl)propylcarbamate

Refernces

• 1、 Chen, Ping,Cheng, Peter T. W.,Spergel, Steven H.,Zahler, Robert,Wang, Xuebao,Thottathil, John,Barrish, Joel C.,Polniaszek, Richard P.. "A practical method for the preparation of α'-chloroketones of N-carbanaate protected-α-aminoacids". . p. 3175 - 3178. Retrieved 2007/10/03.