(S)-2-Acetamido-6-((tert-butoxycarbonyl)amino)hexanoic acid

Base Information

• Chemical Name: (S)-2-Acetamido-6-((tert-butoxycarbonyl)amino)hexanoic acid
• CAS No.: 23500-04-1
• Molecular Formula: C13H24 N2 O5
• Molecular Weight: 288.344
• Hs Code.: 2924199090
• DSSTox Substance ID: DTXSID50427142
• Nikkaji Number: J307.769A
• Wikidata: Q82239860
• Mol file: 23500-04-1.mol

Synonyms:23500-04-1;Ac-Lys(Boc)-OH;(S)-2-Acetamido-6-((tert-butoxycarbonyl)amino)hexanoic acid;(2S)-2-acetamido-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoic acid;Acetyl-Nepsilon-Boc-L-lysine;MFCD00236761;Ac-L-Lys(Boc)-OH;SCHEMBL10254699;Ac-Lys (Boc)-OH, AldrichCPR;DTXSID50427142;AKOS015999018;DS-17079;CS-0154012;(S)-2-Acetamido-6-(BOC-amino)hexanoic acid;N2-Acetyl-N6-(tert-butoxycarbonyl)-L-lysine;F10783;N~2~-Acetyl-N~6~-(tert-butoxycarbonyl)-L-lysine;L-Lysine,n2-acetyl-n6-[(1,1-dimethylethoxy)carbonyl]-;L-Lysine, N2-acetyl-N6-[(1,1-dimethylethoxy)carbonyl]-

Chemical Property of (S)-2-Acetamido-6-((tert-butoxycarbonyl)amino)hexanoic acid

Chemical Property:

• Melting Point: 128 °C
• Boiling Point: 528.8±45.0 °C(Predicted)
• PKA: 3.65±0.10(Predicted)
• PSA: 104.73000
• Density: 1.124±0.06 g/cm3(Predicted)
• LogP: 2.05250
• Storage Temp.: 2-8°C
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 288.16852187
• Heavy Atom Count: 20
• Complexity: 349

Purity/Quality:

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

N-alpha-Acetyl-Nε-Boc-L-lysine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (S)-2-Acetamido-6-((tert-butoxycarbonyl)amino)hexanoic acid

There total 7 articles about (S)-2-Acetamido-6-((tert-butoxycarbonyl)amino)hexanoic acid 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: 87.7%

(S)-2-amino-6-(tert-butoxycarbonylamino)hexanoic acid (2418-95-3) + acetyl chloride (75-36-5) → N2-acetyl-N6-(tert-butyloxycarbonyl)-L-lysine (23500-04-1)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; water; at 0 - 20 ℃; for 4h;

Reference yield: 78.5%

(S)-2-amino-6-(tert-butoxycarbonylamino)hexanoic acid (2418-95-3) + acetic anhydride (108-24-7) → N2-acetyl-N6-(tert-butyloxycarbonyl)-L-lysine (23500-04-1)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; at 20 ℃; for 4h; pH=11;

DOI:10.1021/ol061098a

Reference yield: 32.5%

N-Ac-L-Lys-OH (1946-82-3,152473-69-3) + di-tert-butyl dicarbonate (24424-99-5) → N2-acetyl-N6-(tert-butyloxycarbonyl)-L-lysine (23500-04-1)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; at -10 - 0 ℃; for 4h; pH=11;

DOI:10.1021/ml500192a

upstream raw materials:

(S)-2-amino-6-(tert-butoxycarbonylamino)hexanoic acid

acetic anhydride

di-tert-butyl dicarbonate

L-Lysine hydrochloride

Downstream raw materials:

N²-acetyl-N⁶-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-lysine

N²-acetyl-N⁶-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-lysyl-L-valyl-N⁵-carbamoyl-N-[4-(hydroxymethyl)phenyl]-L-ornithinamide

N²-acetyl-N⁶-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-lysyl-L-valyl-N⁵-carbamoyl-N-[4-({[(4-nitrophenoxy)carbonyl]oxy}methyl)phenyl]-L-ornithinamide

[5-acetylamino-5-[2-(4-sulfamoylphenyl)ethylcarbamoyl]pentyl]carbamic acid tert-butyl ester

Refernces

• 1、 Verhoog, Stefan,Kee, Choon Wee,Wang, Yanlan,Khotavivattana, Tanatorn,Wilson, Thomas C.,Kersemans, Veerle,Smart, Sean,Tredwell, Matthew,Davis, Benjamin G.,Gouverneur, Véronique. "18F-Trifluoromethylation of Unmodified Peptides with 5-18F-(Trifluoromethyl)dibenzothiophenium Trifluoromethanesulfonate". supporting information. p. 1572 - 1575. Retrieved 2018/02/17.
• 2、 Ceruso, Mariangela,Del Prete, Sonia,Alothman, Zeid,Capasso, Clemente,Supuran, Claudiu T.. "Sulfonamides with potent inhibitory action and selectivity against the α-carbonic anhydrase from Vibrio cholerae". . p. 826 - 830. Retrieved 2014/08/05.