[(S)-1-[Hydroxy-((R)-1-phenyl-ethylcarbamoyl)-methyl]-5-(3-methyl-ureido)-pentyl]-carbamic acid 1-(2,6-difluoro-benzyl)-cyclobutylmethyl ester

Base Information

• Chemical Name: [(S)-1-[Hydroxy-((R)-1-phenyl-ethylcarbamoyl)-methyl]-5-(3-methyl-ureido)-pentyl]-carbamic acid 1-(2,6-difluoro-benzyl)-cyclobutylmethyl ester
• CAS No.: 568591-30-0
• Molecular Formula: C₃₀H₄₀F₂N₄O₅
• Molecular Weight: 574.668

Synonyms:

Chemical Property of [(S)-1-[Hydroxy-((R)-1-phenyl-ethylcarbamoyl)-methyl]-5-(3-methyl-ureido)-pentyl]-carbamic acid 1-(2,6-difluoro-benzyl)-cyclobutylmethyl ester

Chemical Property:

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Technology Process of [(S)-1-[Hydroxy-((R)-1-phenyl-ethylcarbamoyl)-methyl]-5-(3-methyl-ureido)-pentyl]-carbamic acid 1-(2,6-difluoro-benzyl)-cyclobutylmethyl ester

There total 10 articles about [(S)-1-[Hydroxy-((R)-1-phenyl-ethylcarbamoyl)-methyl]-5-(3-methyl-ureido)-pentyl]-carbamic acid 1-(2,6-difluoro-benzyl)-cyclobutylmethyl 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:

(R)-(+)-α-methylbenzylisocyanide (17329-20-3,21872-32-2,21872-33-3,42412-74-8) → [(S)-1-[Hydroxy-((R)-1-phenyl-ethylcarbamoyl)-methyl]-5-(3-methyl-ureido)-pentyl]-carbamic acid 1-(2,6-difluoro-benzyl)-cyclobutylmethyl ester (568591-30-0)

Guidance literature:

Multi-step reaction with 6 steps

1: CH₂Cl₂

2: aq. LiOH / dioxane / 100 °C

3: 99 percent / H₂ / Pd/C / ethanol / 2068.59 Torr

4: NEt₃ / tetrahydrofuran

5: 99 percent / HCl(g) / ethyl acetate / 0 °C

6: Et₃N / tetrahydrofuran

With hydrogenchloride; lithium hydroxide; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; ethyl acetate; 1: Passerini reaction;

DOI:10.1016/j.bmcl.2004.07.031

Reference yield:

[(S)-5-tert-Butoxycarbonylamino-6-hydroxy-6-((R)-1-phenyl-ethylcarbamoyl)-hexyl]-carbamic acid benzyl ester (568591-15-1) → [(S)-1-[Hydroxy-((R)-1-phenyl-ethylcarbamoyl)-methyl]-5-(3-methyl-ureido)-pentyl]-carbamic acid 1-(2,6-difluoro-benzyl)-cyclobutylmethyl ester (568591-30-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 99 percent / H₂ / Pd/C / ethanol / 2068.59 Torr

2: NEt₃ / tetrahydrofuran

3: 99 percent / HCl(g) / ethyl acetate / 0 °C

4: Et₃N / tetrahydrofuran

With hydrogenchloride; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; ethyl acetate;

DOI:10.1016/j.bmcl.2004.07.031

Reference yield:

Benzoic acid (S)-6-benzyloxycarbonylamino-2-tert-butoxycarbonylamino-1-((R)-1-phenyl-ethylcarbamoyl)-hexyl ester (568591-14-0) → [(S)-1-[Hydroxy-((R)-1-phenyl-ethylcarbamoyl)-methyl]-5-(3-methyl-ureido)-pentyl]-carbamic acid 1-(2,6-difluoro-benzyl)-cyclobutylmethyl ester (568591-30-0)

Guidance literature:

Multi-step reaction with 5 steps

1: aq. LiOH / dioxane / 100 °C

2: 99 percent / H₂ / Pd/C / ethanol / 2068.59 Torr

3: NEt₃ / tetrahydrofuran

4: 99 percent / HCl(g) / ethyl acetate / 0 °C

5: Et₃N / tetrahydrofuran

With hydrogenchloride; lithium hydroxide; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; ethanol; ethyl acetate;

DOI:10.1016/j.bmcl.2004.07.031

upstream raw materials:

(S)-3-Amino-2-hydroxy-7-(3-methyl-ureido)-heptanoic acid ((R)-1-phenyl-ethyl)-amide

ethyl cyclobutylcarboxylate

2,6-Difluorobenzyl bromide

(R)-(+)-α-methylbenzylisocyanide

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