Z-L-Val-chloromethylketone

Base Information

• Chemical Name: Z-L-Val-chloromethylketone
• CAS No.: 90105-41-2
• Molecular Formula: C14H18 Cl N O3
• Molecular Weight: 283.755
• Mol file: 90105-41-2.mol

Synonyms:Carbamic acid,[(1S)-3-chloro-1-(1-methylethyl)-2-oxopropyl]-, phenylmethyl ester (9CI);Carbamic acid, [3-chloro-1-(1-methylethyl)-2-oxopropyl]-, phenylmethyl ester,(S)-

Chemical Property of Z-L-Val-chloromethylketone

Chemical Property:

• Melting Point: 69-74 °C(Solv: ethanol (64-17-5))
• Boiling Point: 417.6±35.0 °C(Predicted)
• PKA: 10.69±0.46(Predicted)
• PSA: 58.89000
• Density: 1.168±0.06 g/cm3(Predicted)
• LogP: 2.94970

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Z-L-Val-chloromethylketone

There total 10 articles about Z-L-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: 75.0%

dimethylsulfoxonium (3S)-2-oxo-3-(benzyloxycarbonylamino)-4-methylpentylide (850796-29-1) → (S)-1-chloro-3-(benzyloxycarbonylamino)-4-methyl-2-pentanone (90105-41-2)

Guidance literature:

With methanesulfonic acid; lithium chloride; In tetrahydrofuran; at 70 ℃; for 48h;

DOI:10.1021/jo035733r

Reference yield: 74.0%

benzyl (S)-(1-diazo-4-methyl-2-oxopentan-3-yl)carbamate (90105-46-7,28094-73-7) → (S)-1-chloro-3-(benzyloxycarbonylamino)-4-methyl-2-pentanone (90105-41-2)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; diethyl ether; at 5 ℃; for 0.25h;

Reference yield:

Chloroiodomethane (593-71-5) + methyl (2S)-3-methyl-[(benzyloxy)carbonylamino]butanoate (24210-19-3) → (S)-1-chloro-3-(benzyloxycarbonylamino)-4-methyl-2-pentanone (90105-41-2)

Guidance literature:

Chloroiodomethane; methyl (2S)-3-methyl-[(benzyloxy)carbonylamino]butanoate; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 2.5h; Inert atmosphere;

With acetic acid; In tetrahydrofuran; at -70 - 20 ℃;

upstream raw materials:

diazomethane

C₁₆H₂₁NO₅

benzyl (S)-(1-diazo-4-methyl-2-oxopentan-3-yl)carbamate

dimethylsulfoxonium (3S)-2-oxo-3-(benzyloxycarbonylamino)-4-methylpentylide

Downstream raw materials:

Z-Val-CH₂N₃

Z-Ala-ValCH₂Cl

Boc-Tyr-Leu-Val-CH₂Cl

Boc-Tyr-D-Leu-Val-CH₂Cl

Refernces

• 1、 -. "PROCESS FOR THE PREPARATION OF ALPHA-CHLOROKETONES FROM ALKYL ESTERS". Page/Page column 5. . Retrieved 2010/02/11.
• 2、 Tsuda,Okada,Nagamatsu,Okamoto. "Synthesis of peptide chloromethyl ketones and examination of their inhibitory effects on human spleen fibrinolytic proteinase (SFP) and human leukocyte elastase (LE)". . p. 3576 - 3584. Retrieved 2007/10/02.