Boc-leu-chloromethylketone

Base Information

• Chemical Name: Boc-leu-chloromethylketone
• CAS No.: 102123-85-3
• Molecular Formula: C₁₂H₂₂ClNO₃
• Molecular Weight: 263.765
• DSSTox Substance ID: DTXSID80427296
• Wikidata: Q82239981
• Mol file: 102123-85-3.mol

Synonyms:BOC-LEU-CHLOROMETHYLKETONE;102123-85-3;Boc-L-Leu-chloromethylketone;Boc-L-Leucine chloromethylketone;tert-butyl N-[(3S)-1-chloro-5-methyl-2-oxohexan-3-yl]carbamate;(S)-tert-Butyl (1-chloro-5-methyl-2-oxohexan-3-yl)carbamate;Boc-LeuCH2Cl;SCHEMBL6488694;DTXSID80427296;ZNJWTNDBZSOFFP-VIFPVBQESA-N;MFCD00672492;FD21946;AS-49253;CS-0154138;(S)-tert-butyl 1-chloro-5-methyl-2-oxohexan-3-ylcarbamate;(3S)-3-tert-Butoxycarbonylamino-1-chloro-5-methyl-2-hexanone;Carbamic acid,[(1S)-1-(chloroacetyl)-3-methylbutyl]-,1,1-dimethylethyl ester(9ci)

Chemical Property of Boc-leu-chloromethylketone

Chemical Property:

• Melting Point: 64-65 °C
• Boiling Point: 349.6±22.0 °C(Predicted)
• PKA: 10.99±0.46(Predicted)
• PSA: 55.40000
• Density: 1.062±0.06 g/cm3(Predicted)
• LogP: 3.12460
• Storage Temp.: -15°C
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 263.1288213
• Heavy Atom Count: 17
• Complexity: 271

Purity/Quality:

99% ^*data from raw suppliers

Boc-L-leucine chloromethylketone 99+% ^*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)NC(=O)OC(C)(C)C
• Isomeric SMILES: CC(C)C[C@@H](C(=O)CCl)NC(=O)OC(C)(C)C

Technology Process of Boc-leu-chloromethylketone

There total 3 articles about Boc-leu-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: 87.0%

(3S)-3-<(tert-butoxy)carbonylamino>-1-diazo-5-methylhexan-2-one (52716-48-0) → (S)-1-chloro-2-oxo-3-(Boc-amino)-5-methylhexane (102123-85-3)

Guidance literature:

With hydrogenchloride; In diethyl ether;

Reference yield:

N-tert-butoxycarbonyl-L-leucine (13139-15-6,53296-34-7) → (S)-1-chloro-2-oxo-3-(Boc-amino)-5-methylhexane (102123-85-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) isopropenyl chloroformate, di-isopropylethylamine / 1.) ethyl acetate, -10 deg C, 5 min, 2.) diethyl ether, 0 deg C, 30 min

2: 87 percent / 3 M HCl / diethyl ether

With hydrogenchloride; Isopropenyl chloroformate; N-ethyl-N,N-diisopropylamine; In diethyl ether;

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + (C5H9O2)(NHCHCOO)(CH2C3H7)(CO2C2H5) (75899-20-6,148854-05-1) → (S)-1-chloro-2-oxo-3-(Boc-amino)-5-methylhexane (102123-85-3)

Guidance literature:

With hydrogenchloride; Yield given. Multistep reaction; 1.) THF, 4 deg C, overnight, 2.) THF, 0 deg C, 3 h;

DOI:10.1248/cpb.41.2038

upstream raw materials:

diazomethane

(C₅H₉O₂)(NHCHCOO)(CH₂C₃H₇)(CO₂C₂H₅)

(3S)-3-<(tert-butoxy)carbonylamino>-1-diazo-5-methylhexan-2-one

N-tert-butoxycarbonyl-L-leucine

Downstream raw materials:

Leu-chloromethyl ketone hydrochloride

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