[(S)-5-[(S)-3-tert-Butoxy-2-(2-{4-[4-(2-ethyl-imidazol-1-yl)-butyl]-phenyl}-acetylamino)-propionylamino]-5-(2-cyclohexyl-ethylcarbamoyl)-pentyl]-carbamic acid tert-butyl ester

Base Information

• Chemical Name: [(S)-5-[(S)-3-tert-Butoxy-2-(2-{4-[4-(2-ethyl-imidazol-1-yl)-butyl]-phenyl}-acetylamino)-propionylamino]-5-(2-cyclohexyl-ethylcarbamoyl)-pentyl]-carbamic acid tert-butyl ester
• CAS No.: 1026688-12-9
• Molecular Formula: C₄₃H₇₀N₆O₆
• Molecular Weight: 767.065

Synonyms:[(S)-5-[(S)-3-tert-Butoxy-2-(2-{4-[4-(2-ethyl-imidazol-1-yl)-butyl]-phenyl}-acetylamino)-propionylamino]-5-(2-cyclohexyl-ethylcarbamoyl)-pentyl]-carbamic acid tert-butyl ester

Chemical Property of [(S)-5-[(S)-3-tert-Butoxy-2-(2-{4-[4-(2-ethyl-imidazol-1-yl)-butyl]-phenyl}-acetylamino)-propionylamino]-5-(2-cyclohexyl-ethylcarbamoyl)-pentyl]-carbamic acid tert-butyl ester

Chemical Property:

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Technology Process of [(S)-5-[(S)-3-tert-Butoxy-2-(2-{4-[4-(2-ethyl-imidazol-1-yl)-butyl]-phenyl}-acetylamino)-propionylamino]-5-(2-cyclohexyl-ethylcarbamoyl)-pentyl]-carbamic acid tert-butyl ester

There total 6 articles about [(S)-5-[(S)-3-tert-Butoxy-2-(2-{4-[4-(2-ethyl-imidazol-1-yl)-butyl]-phenyl}-acetylamino)-propionylamino]-5-(2-cyclohexyl-ethylcarbamoyl)-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:

methyl 4-iodophenylacetate (63349-52-0) → [(S)-5-[(S)-3-tert-Butoxy-2-(2-{4-[4-(2-ethyl-imidazol-1-yl)-butyl]-phenyl}-acetylamino)-propionylamino]-5-(2-cyclohexyl-ethylcarbamoyl)-pentyl]-carbamic acid tert-butyl ester (1026688-12-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 85 percent / Et₃N, (Ph₃P)2PdCl₂, CuI / acetonitrile / 3.5 h / 0 - 20 °C

2: 94.5 percent / H₂ / 10percent Pd/C / methanol / 2585.7 Torr

3: 71 percent / Ph₃PMe⁽¹⁺⁾*I^(1-) / acetonitrile / 12 h / 0 - 20 °C

4: 85.9 percent / aq. LiOH / methanol / 18 h / Ambient temperature

5: 1.) NaH / 1.) DMF, 5 deg C, 30 min, 2.) DMF, a) 5 deg C, 1.5 h, b) RT, 5 h

6: 1.) HOBt, DCC, 2.) N-methylmorpholine / 1.) CH₂Cl₂, dimethylacetamide, 0 deg C, 1.5 h, 2.) CH₂Cl₂, dimethylacetamide, a) 0 deg C, 1 h, b) RT, 16 h

With 4-methyl-morpholine; bis-triphenylphosphine-palladium(II) chloride; lithium hydroxide; copper(l) iodide; hydrogen; methyl-triphenylphosphonium iodide; sodium hydride; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; acetonitrile;

DOI:10.1021/jm970094w

Reference yield:

methyl 2-(4-(4-hydroxybut-1-yn-1-yl)phenyl)acetate (192804-72-1) → [(S)-5-[(S)-3-tert-Butoxy-2-(2-{4-[4-(2-ethyl-imidazol-1-yl)-butyl]-phenyl}-acetylamino)-propionylamino]-5-(2-cyclohexyl-ethylcarbamoyl)-pentyl]-carbamic acid tert-butyl ester (1026688-12-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 94.5 percent / H₂ / 10percent Pd/C / methanol / 2585.7 Torr

2: 71 percent / Ph₃PMe⁽¹⁺⁾*I^(1-) / acetonitrile / 12 h / 0 - 20 °C

3: 85.9 percent / aq. LiOH / methanol / 18 h / Ambient temperature

4: 1.) NaH / 1.) DMF, 5 deg C, 30 min, 2.) DMF, a) 5 deg C, 1.5 h, b) RT, 5 h

5: 1.) HOBt, DCC, 2.) N-methylmorpholine / 1.) CH₂Cl₂, dimethylacetamide, 0 deg C, 1.5 h, 2.) CH₂Cl₂, dimethylacetamide, a) 0 deg C, 1 h, b) RT, 16 h

With 4-methyl-morpholine; lithium hydroxide; hydrogen; methyl-triphenylphosphonium iodide; sodium hydride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; acetonitrile;

DOI:10.1021/jm970094w

Reference yield:

methyl 4-(4-hydroxy-1-butyl)phenylacetate (164931-20-8) → [(S)-5-[(S)-3-tert-Butoxy-2-(2-{4-[4-(2-ethyl-imidazol-1-yl)-butyl]-phenyl}-acetylamino)-propionylamino]-5-(2-cyclohexyl-ethylcarbamoyl)-pentyl]-carbamic acid tert-butyl ester (1026688-12-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 71 percent / Ph₃PMe⁽¹⁺⁾*I^(1-) / acetonitrile / 12 h / 0 - 20 °C

2: 85.9 percent / aq. LiOH / methanol / 18 h / Ambient temperature

3: 1.) NaH / 1.) DMF, 5 deg C, 30 min, 2.) DMF, a) 5 deg C, 1.5 h, b) RT, 5 h

4: 1.) HOBt, DCC, 2.) N-methylmorpholine / 1.) CH₂Cl₂, dimethylacetamide, 0 deg C, 1.5 h, 2.) CH₂Cl₂, dimethylacetamide, a) 0 deg C, 1 h, b) RT, 16 h

With 4-methyl-morpholine; lithium hydroxide; methyl-triphenylphosphonium iodide; sodium hydride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In methanol; acetonitrile;

DOI:10.1021/jm970094w

upstream raw materials:

4-[4-(2-ethyl-1H-imidazol-1-yl)butyl]phenylacetic acid

methyl 4-iodophenylacetate

4-(4-iodobutyl)phenylacetic acid

methyl 4-(4-hydroxy-1-butyl)phenylacetate

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