3-Amino-1-chloro-5-methylhexan-2-one--hydrogen chloride (1/1)

Base Information

• Chemical Name: 3-Amino-1-chloro-5-methylhexan-2-one--hydrogen chloride (1/1)
• CAS No.: 54518-92-2
• Molecular Formula: C7H14 Cl N O . Cl H
• Molecular Weight: 200.11
• Hs Code.: 2922399090
• DSSTox Substance ID: DTXSID60969725
• NSC Number: 187721
• Mol file: 54518-92-2.mol

Synonyms:DTXSID60969725;3-Amino-1-chloro-5-methylhexan-2-one--hydrogen chloride (1/1);NSC187721;NSC-187721

Chemical Property of 3-Amino-1-chloro-5-methylhexan-2-one--hydrogen chloride (1/1)

Chemical Property:

• PSA: 43.09000
• LogP: 2.67000
• Storage Temp.: -15°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 199.0530695
• Heavy Atom Count: 11
• Complexity: 114

Purity/Quality:

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

L-Leucine chloromethyl ketone hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(C(=O)CCl)N.Cl
• Uses: L-Leucine chloromethyl ketone HCl

Technology Process of 3-Amino-1-chloro-5-methylhexan-2-one--hydrogen chloride (1/1)

There total 2 articles about 3-Amino-1-chloro-5-methylhexan-2-one--hydrogen chloride (1/1) 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:

(S)-1-chloro-2-oxo-3-(Boc-amino)-5-methylhexane (102123-85-3) → Leu-chloromethyl ketone hydrochloride (54518-92-2)

Guidance literature:

With hydrogenchloride; In N,N-dimethyl-formamide; at 0 ℃; for 3h;

DOI:10.1248/cpb.41.2038

Reference yield:

(C5H9O2)(NHCHCOO)(CH2C3H7)(CO2C2H5) (75899-20-6,148854-05-1) → Leu-chloromethyl ketone hydrochloride (54518-92-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.) 7.6N HCl/dioxane / 1.) THF, 4 deg C, overnight, 2.) THF, 0 deg C, 3 h

2: 7.6N HCl/dioxane / dimethylformamide / 3 h / 0 °C

With hydrogenchloride; In N,N-dimethyl-formamide;

DOI:10.1248/cpb.41.2038

Reference yield: 67.2%

Leu-chloromethyl ketone hydrochloride (54518-92-2) + C9H11NO2C5H8O2CO2C4H8 (60398-40-5,67729-36-6) → Boc-D-Phe-Leu-CH2Cl (170028-11-2)

Guidance literature:

With 4-methyl-morpholine; In tetrahydrofuran; N,N-dimethyl-formamide; 0 deg C, 1h; room temp., overnight;

DOI:10.1016/0040-4020(95)00385-L

upstream raw materials:

(S)-1-chloro-2-oxo-3-(Boc-amino)-5-methylhexane

(C₅H₉O₂)(NHCHCOO)(CH₂C₃H₇)(CO₂C₂H₅)

Downstream raw materials:

{(S)-1-[(S)-1-(2-Chloro-acetyl)-3-methyl-butylcarbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester

Boc-D-Phe-Leu-CH₂Cl

(S)-2-[(S)-2-((S)-2-Acetylamino-3-benzyloxy-propionylamino)-4-methyl-pentanoylamino]-N¹-[(S)-1-(2-chloro-acetyl)-3-methyl-butyl]-succinamide

[(S)-2-Benzyloxy-1-((S)-1-{(S)-2-carbamoyl-1-[(S)-1-(2-chloro-acetyl)-3-methyl-butylcarbamoyl]-ethylcarbamoyl}-3-methyl-butylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester

Refernces

• 1、 Taguchi,Yokoi,Tsukatani,Okada. "Amino acids and peptides. XLI. Facile synthesis of 5-methyl-2(1H)-pyrazinone derivatives from dipeptidyl chloromethyl ketones". . p. 7361 - 7372. Retrieved 2007/10/02.