[1,1-Dimethyl-2-((R)-1-{2'-[(3-methyl-ureido)-methyl]-biphenyl-4-ylmethyl}-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-ylcarbamoyl)-ethyl]-carbamic acid benzyl ester

Base Information

• Chemical Name: [1,1-Dimethyl-2-((R)-1-{2'-[(3-methyl-ureido)-methyl]-biphenyl-4-ylmethyl}-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-ylcarbamoyl)-ethyl]-carbamic acid benzyl ester
• CAS No.: 197652-43-0
• Molecular Formula: C₃₉H₄₃N₅O₅
• Molecular Weight: 661.801

Synonyms:[1,1-Dimethyl-2-((R)-1-{2'-[(3-methyl-ureido)-methyl]-biphenyl-4-ylmethyl}-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-ylcarbamoyl)-ethyl]-carbamic acid benzyl ester

Chemical Property of [1,1-Dimethyl-2-((R)-1-{2'-[(3-methyl-ureido)-methyl]-biphenyl-4-ylmethyl}-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-ylcarbamoyl)-ethyl]-carbamic acid benzyl ester

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Technology Process of [1,1-Dimethyl-2-((R)-1-{2'-[(3-methyl-ureido)-methyl]-biphenyl-4-ylmethyl}-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-ylcarbamoyl)-ethyl]-carbamic acid benzyl ester

There total 13 articles about [1,1-Dimethyl-2-((R)-1-{2'-[(3-methyl-ureido)-methyl]-biphenyl-4-ylmethyl}-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-ylcarbamoyl)-ethyl]-carbamic acid benzyl 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:

2,2-dimethylsuccinic acid (597-43-3) → [1,1-Dimethyl-2-((R)-1-{2'-[(3-methyl-ureido)-methyl]-biphenyl-4-ylmethyl}-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-ylcarbamoyl)-ethyl]-carbamic acid benzyl ester (197652-43-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) conc. H₂SO₄, 2.) Et₃N, diphenylphosphoryl azide

2: 99 percent / 2N aq. NaOH / methanol / 16 h / Ambient temperature

3: 94 percent / Et₃N, benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate / CH₂Cl₂ / 2 h / Ambient temperature

4: 1.) NaH / 1.) DMF, 15 min, 2.) DMF, 0 deg C, 15 min

With sodium hydroxide; sulfuric acid; diphenylphosphoranyl azide; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; sodium hydride; triethylamine; In methanol; dichloromethane;

DOI:10.1021/jm970816j

Reference yield:

2-bromobenzylamine hydrochloride (5465-63-4) → [1,1-Dimethyl-2-((R)-1-{2'-[(3-methyl-ureido)-methyl]-biphenyl-4-ylmethyl}-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-ylcarbamoyl)-ethyl]-carbamic acid benzyl ester (197652-43-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) Et₃N / 1.) methylene chloride, 0 deg C, 5 min, 2.) methylene chloride, 2 h

2: 100 percent / 5N aq. NaOH, Pd(PPh₃)4 / benzene; propan-2-ol / 2 h / Heating

3: 92 percent / Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

4: Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

5: anisole / CH₂Cl₂ / 1.5 h / Ambient temperature

6: CH₂Cl₂ / 0.5 h / Ambient temperature

7: 95 percent / LiOH / tetrahydrofuran; H₂O / 16 h / Ambient temperature

8: 100 percent / Et₃N / CH₂Cl₂; dimethylformamide / 0.5 h / 0 °C

9: 1.) NaH / 1.) DMF, 15 min, 2.) DMF, 0 deg C, 15 min

With lithium hydroxide; sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; sodium hydride; methoxybenzene; triethylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; benzene;

DOI:10.1021/jm970816j

Reference yield:

(R)-3-amino-2,3,4,5-tetrahydro-1H-[1]-benzazepin-2-one (137036-55-6) → [1,1-Dimethyl-2-((R)-1-{2'-[(3-methyl-ureido)-methyl]-biphenyl-4-ylmethyl}-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-ylcarbamoyl)-ethyl]-carbamic acid benzyl ester (197652-43-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / Et₃N, benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate / CH₂Cl₂ / 2 h / Ambient temperature

2: 1.) NaH / 1.) DMF, 15 min, 2.) DMF, 0 deg C, 15 min

With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; sodium hydride; triethylamine; In dichloromethane;

DOI:10.1021/jm970816j

upstream raw materials:

2,2-dimethylsuccinic acid

2-bromobenzylamine hydrochloride

(R)-3-amino-2,3,4,5-tetrahydro-1H-[1]-benzazepin-2-one

4-hydroxymethyl-2'(t-butoxycarbonylaminomethyl)-1,1'-biphenyl

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