N-(2,3-Dimethylphenyl)-2(S)-(tert butoxycarbonylamino)hexanamine

Base Information

• Chemical Name: N-(2,3-Dimethylphenyl)-2(S)-(tert butoxycarbonylamino)hexanamine
• CAS No.: 186203-16-7
• Molecular Formula: C₁₉H₃₂N₂O₂
• Molecular Weight: 320.475
• DSSTox Substance ID: DTXSID601120687
• Mol file: 186203-16-7.mol

Synonyms:SCHEMBL7567629;ADQCHZRAISAVTI-INIZCTEOSA-N;DTXSID601120687;N-(2,3-Dimethylphenyl)-2(S)-(tert butoxycarbonylamino)hexanamine;N-(2,3-Dimethylphenyl)-2(S)-(tert-butoxycarbonylamino) hexanamine;N-(2,3-Dimethylphenyl)-2(S)-(tert-butoxycarbonylamino)-hexanamine;186203-16-7;Carbamic acid, [(1S)-1-[[(2,3-dimethylphenyl)amino]methyl]pentyl]-, 1,1-dimethylethyl ester

Chemical Property of N-(2,3-Dimethylphenyl)-2(S)-(tert butoxycarbonylamino)hexanamine

Chemical Property:

• XLogP3: 5.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 9
• Exact Mass: 320.246378268
• Heavy Atom Count: 23
• Complexity: 352

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCC(CNC1=CC=CC(=C1C)C)NC(=O)OC(C)(C)C
• Isomeric SMILES: CCCC[C@@H](CNC1=CC=CC(=C1C)C)NC(=O)OC(C)(C)C

Technology Process of N-(2,3-Dimethylphenyl)-2(S)-(tert butoxycarbonylamino)hexanamine

There total 4 articles about N-(2,3-Dimethylphenyl)-2(S)-(tert butoxycarbonylamino)hexanamine 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: 63.0%

(S)-N-Boc-leucinal (104062-70-6,440125-24-6) + 2,3-Dimethylaniline (87-59-2) → N-(2,3-Dimethylphenyl)-2(S)-(tert-butoxycarbonylamino) hexanamine (186203-16-7)

Guidance literature:

With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20 ℃; pH=6;

DOI:10.1021/jm990254z

Reference yield:

Boc-Nle-OH (6404-28-0) → N-(2,3-Dimethylphenyl)-2(S)-(tert-butoxycarbonylamino) hexanamine (186203-16-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / EDC; HOBT; Et₃N / dimethylformamide

2: 100 percent / LiAlH₄

3: 63 percent / NaBH(OAc)3 / 1,2-dichloro-ethane / 20 °C / pH 6

With lithium aluminium tetrahydride; sodium tris(acetoxy)borohydride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1: Acylation / 2: Reduction / 3: reductive alkylation;

DOI:10.1021/jm990254z

Reference yield:

N-Methoxy-N-methyl 2(S)-(tert-butoxycarbonylamino) hexanamide (104062-69-3) → N-(2,3-Dimethylphenyl)-2(S)-(tert-butoxycarbonylamino) hexanamine (186203-16-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / LiAlH₄

2: 63 percent / NaBH(OAc)3 / 1,2-dichloro-ethane / 20 °C / pH 6

With lithium aluminium tetrahydride; sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; 1: Reduction / 2: reductive alkylation;

DOI:10.1021/jm990254z

upstream raw materials:

(S)-N-Boc-leucinal

2,3-Dimethylaniline

Boc-Nle-OH

N-Methoxy-N-methyl 2(S)-(tert-butoxycarbonylamino) hexanamide

Downstream raw materials:

4-tert-Butoxycarbonyl-5(S)-n-butyl-1-(2,3-dimethylphenyl)piperazin-2-one

5(S)-n-Butyl-1-(2,3-dimethylphenyl)-2-piperazinone

((S)-1-{[(2-Chloro-acetyl)-(2,3-dimethyl-phenyl)-amino]-methyl}-pentyl)-carbamic acid tert-butyl ester