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

Base Information

• Chemical Name: [1-Methyl-1-((R)-1-{2'-[2-(3-methyl-ureido)-ethyl]-biphenyl-4-ylmethyl}-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-ylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester
• CAS No.: 197652-61-2
• Molecular Formula: C₃₆H₄₅N₅O₅
• Molecular Weight: 627.784

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

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

Chemical Property:

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

There total 9 articles about [1-Methyl-1-((R)-1-{2'-[2-(3-methyl-ureido)-ethyl]-biphenyl-4-ylmethyl}-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-ylcarbamoyl)-ethyl]-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:

Boc-Aib-OH (30992-29-1) → [1-Methyl-1-((R)-1-{2'-[2-(3-methyl-ureido)-ethyl]-biphenyl-4-ylmethyl}-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-ylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester (197652-61-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / Et₃N, benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate / CH₂Cl₂ / 2 h / Ambient temperature

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

With sodium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In dichloromethane;

DOI:10.1021/jm970816j

Reference yield:

2-(2-bromophenyl)acetonitrile (19472-74-3) → [1-Methyl-1-((R)-1-{2'-[2-(3-methyl-ureido)-ethyl]-biphenyl-4-ylmethyl}-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-ylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester (197652-61-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 73 percent / Pd(PPh₃)4, tripotassium phosphate / dimethylformamide / 3 h / 100 °C

2: Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

3: 100 percent / imidazole / dimethylformamide / 1.) 0 deg C, 15 min, 2.) RT, 16 h

4: 1.) Bu₄NBH₄, 2.) 10percent aq. HCl / 1.) CH₂Cl₂, reflux, 9 h, 2.) THF, reflux, 1 h

5: Et₃N / CH₂Cl₂ / 0.5 h / Ambient temperature

6: Et₃N / CH₂Cl₂; dimethylformamide / 0.5 h / 0 °C

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

With 1H-imidazole; hydrogenchloride; potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; sodium hydride; tetrabutylammonium borohydride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm970816j

Reference yield:

4-(tert-butyldiphenylsiloxymethyl)phenylboronic acid → [1-Methyl-1-((R)-1-{2'-[2-(3-methyl-ureido)-ethyl]-biphenyl-4-ylmethyl}-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-ylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester (197652-61-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 73 percent / Pd(PPh₃)4, tripotassium phosphate / dimethylformamide / 3 h / 100 °C

2: Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

3: 100 percent / imidazole / dimethylformamide / 1.) 0 deg C, 15 min, 2.) RT, 16 h

4: 1.) Bu₄NBH₄, 2.) 10percent aq. HCl / 1.) CH₂Cl₂, reflux, 9 h, 2.) THF, reflux, 1 h

5: Et₃N / CH₂Cl₂ / 0.5 h / Ambient temperature

6: Et₃N / CH₂Cl₂; dimethylformamide / 0.5 h / 0 °C

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

With 1H-imidazole; hydrogenchloride; potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; sodium hydride; tetrabutylammonium borohydride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm970816j

upstream raw materials:

Boc-Aib-OH

2-(2-bromophenyl)acetonitrile

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

2'-(2-aminoethyl)-1,1'-biphenyl-4-methanol

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