(3RS)-1-cyclohexylcarbonylmethyl-3-[N-tert-butoxycarbonyl-(S)-phenylalanyl]amino-5-ethyl-2,3-dihydro-9-methyl-1H-1,4-benzodiazepin-2-one

Base Information

Chemical Name:(3RS)-1-cyclohexylcarbonylmethyl-3-[N-tert-butoxycarbonyl-(S)-phenylalanyl]amino-5-ethyl-2,3-dihydro-9-methyl-1H-1,4-benzodiazepin-2-one
CAS No.:205998-78-3
Molecular Formula:C₃₄H₄₄N₄O₅
Molecular Weight:588.747
Hs Code.:

Synonyms:(3RS)-1-cyclohexylcarbonylmethyl-3-[N-tert-butoxycarbonyl-(S)-phenylalanyl]amino-5-ethyl-2,3-dihydro-9-methyl-1H-1,4-benzodiazepin-2-one

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Chemical Property of (3RS)-1-cyclohexylcarbonylmethyl-3-[N-tert-butoxycarbonyl-(S)-phenylalanyl]amino-5-ethyl-2,3-dihydro-9-methyl-1H-1,4-benzodiazepin-2-one

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Technology Process of (3RS)-1-cyclohexylcarbonylmethyl-3-[N-tert-butoxycarbonyl-(S)-phenylalanyl]amino-5-ethyl-2,3-dihydro-9-methyl-1H-1,4-benzodiazepin-2-one

There total 6 articles about (3RS)-1-cyclohexylcarbonylmethyl-3-[N-tert-butoxycarbonyl-(S)-phenylalanyl]amino-5-ethyl-2,3-dihydro-9-methyl-1H-1,4-benzodiazepin-2-one 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: 100.0%

: 13734-34-4
N-tert-butoxycarbonyl-L-phenylalanine

: 205996-41-4
(3RS)-3-amino-1-cyclohexyl-carbonylmethyl-2,3-dihydro-5-ethyl-9-methyl-1H-1,4-benzodiazepin-2-one

: 205998-78-3
(3RS)-1-cyclohexylcarbonylmethyl-3-[N-tert-butoxycarbonyl-(S)-phenylalanyl]amino-5-ethyl-2,3-dihydro-9-methyl-1H-1,4-benzodiazepin-2-one

Guidance literature:: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20 ℃;
DOI:10.1248/cpb.48.1

Reference yield:

: 95-53-4
o-toluidine

: 205998-78-3
(3RS)-1-cyclohexylcarbonylmethyl-3-[N-tert-butoxycarbonyl-(S)-phenylalanyl]amino-5-ethyl-2,3-dihydro-9-methyl-1H-1,4-benzodiazepin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: BCl₃ / toluene / 1 h / 20 °C

1.2: AlCl₃ / acetonitrile / 5 h / Heating

1.3: 64.5 percent / 2 N aq. HCl / acetonitrile / 2.5 h / Heating

2.1: N-methylmorpholine / tetrahydrofuran / 0 - 20 °C

3.1: NH₃ / methanol / 20 °C

4.1: NaH / dimethylformamide / 4 h / 0 - 20 °C

4.2: 41.2 percent / dimethylformamide / 5.5 h / 20 °C

5.1: 100 percent / ammonium formate / 10 percent Pd/C / ethanol / 1 h / 20 °C

6.1: 100 percent / N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide hydrochloride; 1-hydroxybenzotriazole / dimethylformamide / 20 °C

With 4-methyl-morpholine; ammonia; ammonium formate; boron trichloride; sodium hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide; toluene; 1.1: Addition / 1.2: Rearrangement / 1.3: Hydrolysis / 2.1: Acylation / 3.1: Cyclization / 4.1: deprotonation / 4.2: Alkylation / 5.1: Hydrogenolysis / 6.1: Acylation;
DOI:10.1248/cpb.48.1

Reference yield:

: 62819-85-6
2-amino-3-methyl-propiophenone

: 205998-78-3
(3RS)-1-cyclohexylcarbonylmethyl-3-[N-tert-butoxycarbonyl-(S)-phenylalanyl]amino-5-ethyl-2,3-dihydro-9-methyl-1H-1,4-benzodiazepin-2-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: N-methylmorpholine / tetrahydrofuran / 0 - 20 °C

2.1: NH₃ / methanol / 20 °C

3.1: NaH / dimethylformamide / 4 h / 0 - 20 °C

3.2: 41.2 percent / dimethylformamide / 5.5 h / 20 °C

4.1: 100 percent / ammonium formate / 10 percent Pd/C / ethanol / 1 h / 20 °C

5.1: 100 percent / N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide hydrochloride; 1-hydroxybenzotriazole / dimethylformamide / 20 °C

With 4-methyl-morpholine; ammonia; ammonium formate; sodium hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide; 1.1: Acylation / 2.1: Cyclization / 3.1: deprotonation / 3.2: Alkylation / 4.1: Hydrogenolysis / 5.1: Acylation;
DOI:10.1248/cpb.48.1