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

Base Information

• Chemical Name: ((S)-1-{[(2-Chloro-acetyl)-(2,3-dimethyl-phenyl)-amino]-methyl}-pentyl)-carbamic acid tert-butyl ester
• CAS No.: 247593-34-6
• Molecular Formula: C₂₁H₃₃ClN₂O₃
• Molecular Weight: 396.958
• Mol file: 247593-34-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about ((S)-1-{[(2-Chloro-acetyl)-(2,3-dimethyl-phenyl)-amino]-methyl}-pentyl)-carbamic acid tert-butyl ester 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:

chloroacetyl chloride (79-04-9) + N-(2,3-Dimethylphenyl)-2(S)-(tert-butoxycarbonylamino) hexanamine (186203-16-7) → ((S)-1-{[(2-Chloro-acetyl)-(2,3-dimethyl-phenyl)-amino]-methyl}-pentyl)-carbamic acid tert-butyl ester (247593-34-6)

Guidance literature:

With sodium hydrogencarbonate; In ethyl acetate; at 0 ℃;

DOI:10.1021/jm990254z

Reference yield:

(S)-N-Boc-leucinal (104062-70-6,440125-24-6) → ((S)-1-{[(2-Chloro-acetyl)-(2,3-dimethyl-phenyl)-amino]-methyl}-pentyl)-carbamic acid tert-butyl ester (247593-34-6)

Guidance literature:

Multi-step reaction with 2 steps

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

2: aq. NaHCO₃ / ethyl acetate / 0 °C

With sodium tris(acetoxy)borohydride; sodium hydrogencarbonate; In ethyl acetate; 1,2-dichloro-ethane; 1: reductive alkylation / 2: Acylation;

DOI:10.1021/jm990254z

Reference yield:

Boc-Nle-OH (6404-28-0) → ((S)-1-{[(2-Chloro-acetyl)-(2,3-dimethyl-phenyl)-amino]-methyl}-pentyl)-carbamic acid tert-butyl ester (247593-34-6)

Guidance literature:

Multi-step reaction with 4 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

4: aq. NaHCO₃ / ethyl acetate / 0 °C

With lithium aluminium tetrahydride; sodium tris(acetoxy)borohydride; sodium hydrogencarbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1: Acylation / 2: Reduction / 3: reductive alkylation / 4: Acylation;

DOI:10.1021/jm990254z

upstream raw materials:

chloroacetyl chloride

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

(S)-N-Boc-leucinal

Boc-Nle-OH

Downstream raw materials:

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

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