(S)-2-Amino-6-benzamidohexanoic acid

Base Information

• Chemical Name: (S)-2-Amino-6-benzamidohexanoic acid
• CAS No.: 1219-46-1
• Molecular Formula: C13H18 N2 O3
• Molecular Weight: 250.298
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID80924013
• Nikkaji Number: J304.050J
• Mol file: 1219-46-1.mol

Synonyms:1219-46-1;N-epsilon-Benzoyl-L-lysine;(S)-2-Amino-6-benzamidohexanoic acid;(2S)-2-amino-6-benzamidohexanoic acid;Nepsilon-Benzoyl-L-lysine;n6-benzoyl lysine;N6-Benzoyl-L-lysine;Nepsilon -Benzoyl-L-lysine;SCHEMBL1242961;DTXSID80924013;(S)-2-Amino-6-benzamidohexanoicacid;N~6~-[Hydroxy(phenyl)methylidene]lysine;BS-21233;CS-0207344;(2~{S})-2-azanyl-6-benzamido-hexanoic acid;C80044;(2S)-2-AMINO-6-(PHENYLFORMAMIDO)HEXANOIC ACID

Chemical Property of (S)-2-Amino-6-benzamidohexanoic acid

Chemical Property:

• Vapor Pressure: 1.1E-11mmHg at 25°C
• Melting Point: 251-256oC
• Boiling Point: 521°Cat760mmHg
• Flash Point: 268.9°C
• PSA: 92.42000
• Density: 1.186g/cm³
• LogP: 2.08980
• XLogP3: -1.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 250.13174244
• Heavy Atom Count: 18
• Complexity: 275

Purity/Quality:

98%min ^*data from raw suppliers

2-Amino-6-(benzoylamino)hexanoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)NCCCCC(C(=O)O)N
• Isomeric SMILES: C1=CC=C(C=C1)C(=O)NCCCC[C@@H](C(=O)O)N

Technology Process of (S)-2-Amino-6-benzamidohexanoic acid

There total 20 articles about (S)-2-Amino-6-benzamidohexanoic 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: 86.4%

L-lysine (56-87-1,3506-25-0) + N-{2-[(4aR,6S,8aR)-2-(benzoylamino)-6-methyl-4,4a,5,6-tetrahydropyrano[3,4-d][1,3]thiazin-8a(8H)-yl]-1,3-thiazol-4-yl}-5-(difluoromethoxy)pyridine-2-carboxamide → N6-benzoyl-L-lysine (1219-46-1) + N-{2-[(4aR,6S,8aR)-2-amino-6-methyl-4,4a,5,6-tetrahydropyrano[3,4-d][1,3]thiazin-8a(8H)-yl]-1,3-thiazol-4-yl}-5-(difluoromethoxy)pyridine-2-carboxamide

Guidance literature:

In propan-1-ol; water; at 90 ℃; for 24h; Inert atmosphere; Large scale;

DOI:10.1021/acs.oprd.1c00126

Reference yield: 82.0%

Copper(II); (S)-2-amino-6-benzoylamino-hexanoate → N6-benzoyl-L-lysine (1219-46-1)

Guidance literature:

With sodium sulfide; In water; at 25 - 30 ℃; for 0.166667h;

DOI:10.1016/j.tetlet.2006.05.069

Reference yield: 65.0%

L-lysine (56-87-1,3506-25-0) + phenyl(2-thioxothiazolidin-3-yl)methanone (70326-37-3) → N6-benzoyl-L-lysine (1219-46-1)

Guidance literature:

In tetrahydrofuran; water; for 0.05h; Ambient temperature;

DOI:10.1246/cl.1981.463

upstream raw materials:

N²-acetyl-N⁶-benzoyl-DL-lysine

N⁶-benzoyl-N²-chloroacetyl-DL-lysine

N⁶-benzoyl-N²-butyryl-DL-lysine

Nα,ε-dibenzoyl-D,L-lysine

Downstream raw materials:

(S)-2-bromo-6-benzamino-hexanoic acid-⁽¹⁾

N⁶-benzoyl-N²-butyryl-L-lysine

N^α-benzenesulfonyl-N^ε-benzoyl-L-lysine

N^α-(2.4-dinitro-phenyl)-L-lysine

Refernces

• 1、 Venteicher, Brooklynn,Merklin, Kasey,Ngo, Huy X.,Chien, Huan-Chieh,Hutchinson, Keino,Campbell, Jerome,Way, Hannah,Griffith, Joseph,Alvarado, Cesar,Chandra, Surabhi,Hill, Evan,Schlessinger, Avner,Thomas, Allen A.. "The Effects of Prodrug Size and a Carbonyl Linker on l-Type Amino Acid Transporter 1-Targeted Cellular and Brain Uptake". . p. 869 - 880. Retrieved 2020/12/15.
• 2、 Nowshuddin, Shaik,Reddy, A. Ram. "Decomposition of copper-amino acid complexes by sodium sulfide". . p. 5159 - 5161. Retrieved 2007/10/03.