(S)-6-((tert-Butoxycarbonyl)amino)-2-(4-methylphenylsulfonamido)hexanoic acid

Base Information

• Chemical Name: (S)-6-((tert-Butoxycarbonyl)amino)-2-(4-methylphenylsulfonamido)hexanoic acid
• CAS No.: 16948-09-7
• Molecular Formula: C18H28 N2 O6 S
• Molecular Weight: 400.496
• Hs Code.: 2935009090
• DSSTox Substance ID: DTXSID00388456
• ChEMBL ID: CHEMBL181525
• Mol file: 16948-09-7.mol

Synonyms:16948-09-7;TOS-LYS(BOC)-OH;(S)-6-((tert-Butoxycarbonyl)amino)-2-(4-methylphenylsulfonamido)hexanoic acid;(2S)-2-[(4-methylphenyl)sulfonylamino]-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoic acid;C18H28N2O6S;Nalpha-Tosyl-Nepsilon-Boc-L-lysine;Lysine derivative 2;Tosyl-N-epsilon-Boc-L-lysine;BDBM9849;CHEMBL181525;DTXSID00388456;MFCD00237288;AS-46839;CS-0447819;N6-(tert-butoxycarbonyl)-N2-tosyl-L-lysine;F10684;(2S)-6-(tert-butoxycarbonylamino)-2-(p-tolylsulfonylamino)hexanoic acid;(S)-6-(tert-butoxycarbonylamino)-2-(4-methylphenylsulfonamido)hexanoic acid;N~6~-(tert-Butoxycarbonyl)-N~2~-(4-methylbenzene-1-sulfonyl)-L-lysine;Nalpha-(4-methylbenzenesulfonyl)-Nepsilon-tert-butoxycarbonyl-L-lysine;(2S)-6-{[(tert-butoxy)carbonyl]amino}-2-[(4-methylbenzene)sulfonamido]hexanoic acid;L-Lysine, N6-[(1,1-dimethylethoxy)carbonyl]-N2-[(4-methylphenyl)sulfonyl]-

Chemical Property of (S)-6-((tert-Butoxycarbonyl)amino)-2-(4-methylphenylsulfonamido)hexanoic acid

Chemical Property:

• PSA: 133.67000
• LogP: 4.09760
• Storage Temp.: Store at RT.
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 11
• Exact Mass: 400.16680779
• Heavy Atom Count: 27
• Complexity: 586

Purity/Quality:

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

Tos-Lys(Boc)-OH 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)NC(CCCCNC(=O)OC(C)(C)C)C(=O)O
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)N[C@@H](CCCCNC(=O)OC(C)(C)C)C(=O)O

Technology Process of (S)-6-((tert-Butoxycarbonyl)amino)-2-(4-methylphenylsulfonamido)hexanoic acid

There total 4 articles about (S)-6-((tert-Butoxycarbonyl)amino)-2-(4-methylphenylsulfonamido)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: 100.0%

(S)-6-tert-Butoxycarbonylamino-2-(toluene-4-sulfonylamino)-hex-4-ynoic acid (191858-87-4) → Nα-(4-methylbenzenesulfonyl)-Nε-tert-butoxycarbonyl-L-lysine (16948-09-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 21h; under 760 Torr; Ambient temperature;

DOI:10.1002/(SICI)1099-1344(199705)39:5<379::AID-JLCR981>3.0.CO;2-I

Reference yield: 63.0%

(S)-2-amino-6-(tert-butoxycarbonylamino)hexanoic acid (2418-95-3) + p-toluenesulfonyl chloride (98-59-9) → Nα-(4-methylbenzenesulfonyl)-Nε-tert-butoxycarbonyl-L-lysine (16948-09-7)

Guidance literature:

With triethylamine; In water; N,N-dimethyl-formamide; pH 9;

DOI:10.1248/cpb.33.2137

Reference yield:

1-amino-1-(S)-carboxy-5-(t-butoxycarbonyl amino)-3-pentyne (77369-64-3) → Nα-(4-methylbenzenesulfonyl)-Nε-tert-butoxycarbonyl-L-lysine (16948-09-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 51 percent / 2.5N aq. NaOH / 22.5 h / Ambient temperature

2: 100 percent / H₂ / 10percent Pd/C / ethyl acetate / 21 h / 760 Torr / Ambient temperature

With sodium hydroxide; hydrogen; palladium on activated charcoal; In ethyl acetate;

DOI:10.1002/(SICI)1099-1344(199705)39:5<379::AID-JLCR981>3.0.CO;2-I

upstream raw materials:

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

p-toluenesulfonyl chloride

(S)-6-tert-Butoxycarbonylamino-2-(toluene-4-sulfonylamino)-hex-4-ynoic acid

1-amino-1-(S)-carboxy-5-(t-butoxycarbonyl amino)-3-pentyne

Refernces

• 1、 Villani,Heys. "The novel synthesis of the protease inhibitor (S)-1-chloro-3-[(p-tolylsulfonyl)amino]-7-amino-2-[5,5,6,6-3H]heptanone ([3H]T:CK labeled to high specific activity with tritium". . p. 379 - 386. Retrieved 2007/10/03.