(R)-α-amino-N-(2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)benzenepropanamide

Base Information

• Chemical Name: (R)-α-amino-N-(2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)benzenepropanamide
• CAS No.: 108896-03-3
• Molecular Formula: C₂₅H₂₄N₄O₂
• Molecular Weight: 412.491
• Mol file: 108896-03-3.mol

Synonyms:

Chemical Property of (R)-α-amino-N-(2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)benzenepropanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-α-amino-N-(2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)benzenepropanamide

There total 11 articles about (R)-α-amino-N-(2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)benzenepropanamide 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:

1,1-dimethylethyl<(R)-2-<(2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)amino>-2-oxo-1-(phenylmethyl)ethyl>carbamate (103343-62-0,103407-33-6,103432-07-1,108896-01-1,108896-05-5) → (R)-α-amino-N-(2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)benzenepropanamide (103343-63-1,103343-64-2,108896-03-3)

Guidance literature:

With hydrogenchloride; In ethyl acetate; at 0 ℃; for 0.5h;

DOI:10.1021/jo00391a010

Reference yield:

2'-benzoyl-2-bromo-acetanilide (14439-71-5) → (R)-α-amino-N-(2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)benzenepropanamide (103343-63-1,103343-64-2,108896-03-3)

Guidance literature:

Multi-step reaction with 6 steps

1: NH₃ / methanol / 2 h / Heating

2: 93 percent / Aliquat 336, 50percent aq. NaOH / toluene / 4 h / 20 - 25 °C

3: 81.6 percent / t-BuOK, isoamyl nitrite / toluene / 0.5 h / -20 - 0 °C

4: H₂ / 5percent Ru/C / methanol / 24 h / 68 - 74 °C / 2068.6 Torr

5: 90 g / 1-hydroxybenzotriazole, 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride, triethylamine / dimethylformamide / 0.25 h / pH = 9.5

6: HCl(g) / ethyl acetate / 0.5 h / 0 °C

With hydrogenchloride; sodium hydroxide; potassium tert-butylate; ammonia; hydrogen; Aliquat 336; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; isopentyl nitrite; Ru-carbon; In methanol; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00391a010

Reference yield:

1,3-dihydro-1-methyl-3-oximido-5-phenyl-2H-1,4-benzodiazepin-2-one (103373-62-2) → (R)-α-amino-N-(2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)benzenepropanamide (103343-63-1,103343-64-2,108896-03-3)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / 5percent Ru/C / methanol / 24 h / 68 - 74 °C / 2068.6 Torr

2: 90 g / 1-hydroxybenzotriazole, 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride, triethylamine / dimethylformamide / 0.25 h / pH = 9.5

3: HCl(g) / ethyl acetate / 0.5 h / 0 °C

With hydrogenchloride; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; Ru-carbon; In methanol; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo00391a010

upstream raw materials:

1,1-dimethylethyl<(R)-2-<(2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)amino>-2-oxo-1-(phenylmethyl)ethyl>carbamate

Boc-D-Phe-OH

[(R)-1-(2-Oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-ylcarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester

3-amino-5-phenyl-1,3-dihydrobenzo[e][1,4]diazepin-2-one

Downstream raw materials:

(S)-3-amino-1-methyl-5-phenyl-1H-benzo[e][1,4]diazepin-2(3H)-one

(3R)-3-amino-1-methyl-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one