benzyl {trans-(2S)-2-[2-(octanoylamino)cyclopropyloxy]propionyl}-L-alanyl-D-isoglutaminate

Base Information

• Chemical Name: benzyl {trans-(2S)-2-[2-(octanoylamino)cyclopropyloxy]propionyl}-L-alanyl-D-isoglutaminate
• CAS No.: 682747-40-6
• Molecular Formula: C₂₉H₄₄N₄O₇
• Molecular Weight: 560.691
• Mol file: 682747-40-6.mol

Synonyms:benzyl {trans-(2S)-2-[2-(octanoylamino)cyclopropyloxy]propionyl}-L-alanyl-D-isoglutaminate

Chemical Property of benzyl {trans-(2S)-2-[2-(octanoylamino)cyclopropyloxy]propionyl}-L-alanyl-D-isoglutaminate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl {trans-(2S)-2-[2-(octanoylamino)cyclopropyloxy]propionyl}-L-alanyl-D-isoglutaminate

There total 11 articles about benzyl {trans-(2S)-2-[2-(octanoylamino)cyclopropyloxy]propionyl}-L-alanyl-D-isoglutaminate 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: 79.0%

n-octanoic acid chloride (111-64-8) + benzyl N-{trans-(2S)-2-[2-(tert-butoxycarbonylamino)cyclopropyloxy]propionyl}-L-alanyl-D-isoglutaminate (682747-33-7) → benzyl {trans-(2S)-2-[2-(octanoylamino)cyclopropyloxy]propionyl}-L-alanyl-D-isoglutaminate (682747-40-6)

Guidance literature:

benzyl N-{trans-(2S)-2-[2-(tert-butoxycarbonylamino)cyclopropyloxy]propionyl}-L-alanyl-D-isoglutaminate; With hydrogenchloride; In ethyl acetate; for 3h;

n-octanoic acid chloride; With triethylamine; In dichloromethane; at 25 ℃; for 14h; Further stages.;

DOI:10.1016/j.tet.2004.01.037

Reference yield: 63.0%

n-octanoic acid chloride (111-64-8) + benzyl N-{cis-(2S)-2-[2-(tert-butoxycarbonylamino)cyclopropyloxy]propionyl}-L-alanyl-D-isoglutaminate (682747-33-7) → benzyl {cis-(2S)-2-[2-(octanoylamino)cyclopropyloxy]propionyl}-L-alanyl-D-isoglutaminate (682747-40-6)

Guidance literature:

benzyl N-{cis-(2S)-2-[2-(tert-butoxycarbonylamino)cyclopropyloxy]propionyl}-L-alanyl-D-isoglutaminate; With hydrogenchloride; In ethyl acetate; for 3h;

n-octanoic acid chloride; With triethylamine; In dichloromethane; at 25 ℃; for 14h; Further stages.;

DOI:10.1016/j.tet.2004.01.037

Reference yield:

isopropyl (2S)-2-(vinyloxy)propanoate (682747-28-0) → benzyl {trans-(2S)-2-[2-(octanoylamino)cyclopropyloxy]propionyl}-L-alanyl-D-isoglutaminate (682747-40-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 28 percent / [(Rh(OAc)2)2] / CH₂Cl₂ / 8 h / 25 °C

2.1: CF₃COOH / CH₂Cl₂ / 18 h

3.1: 14 percent / DPPA; triethylamine / 3 h / 80 °C

4.1: KOH; ethanol / 3 h / 25 °C

5.1: isobutyl chloroformate; N-methyl-morpholine / ethyl acetate; dimethylformamide / 0.08 h / -15 °C

5.2: 90 percent / N-methyl-morpholine / ethyl acetate; dimethylformamide / 18 h

6.1: hydrochloric acid / ethyl acetate / 3 h

6.2: 79 percent / Et₃N / CH₂Cl₂ / 14 h / 25 °C

With 4-methyl-morpholine; hydrogenchloride; dirhodium tetraacetate; potassium hydroxide; ethanol; diphenyl-phosphinic acid; triethylamine; trifluoroacetic acid; isobutyl chloroformate; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2004.01.037

upstream raw materials:

n-octanoic acid chloride

benzyl N-{cis-(2S)-2-[2-(tert-butoxycarbonylamino)cyclopropyloxy]propionyl}-L-alanyl-D-isoglutaminate

L-alanyl-D-isoglutamine benzyl ester hydrochloride

isopropyl cis-(2S)-2-[2-(tert-butoxycarbonyl)cyclopropyl]oxy-propanoate