tert-butyl N-(2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepin-3-yl)carbamate

Base Information

• Chemical Name: tert-butyl N-(2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepin-3-yl)carbamate
• CAS No.: 168162-29-6
• Molecular Formula: C20H21N3O3
• Molecular Weight: 351.405
• DSSTox Substance ID: DTXSID601130307
• Mol file: 168162-29-6.mol

Synonyms:SCHEMBL644153;DTXSID601130307;tert-butyl N-(2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepin-3-yl)carbamate;(2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)carbamic acid;1,1-Dimethylethyl N-(2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)carbamate;168162-29-6

Chemical Property of tert-butyl N-(2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepin-3-yl)carbamate

Chemical Property:

• XLogP3: 3.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 351.15829154
• Heavy Atom Count: 26
• Complexity: 561

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC1C(=O)NC2=CC=CC=C2C(=N1)C3=CC=CC=C3

Technology Process of tert-butyl N-(2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepin-3-yl)carbamate

There total 6 articles about tert-butyl N-(2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepin-3-yl)carbamate 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:

benzyl 2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-ylcarbamate (108895-98-3) → (2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)carbamic acid tert-butyl ester (168162-29-6)

Guidance literature:

Multi-step reaction with 2 steps

1: Pd(OAc)2; TEA; triethylsilane / CH₂Cl₂ / 3 h / 20 °C

2: 3.78 g / CH₂Cl₂ / 2 h / 20 °C

With triethylsilane; palladium diacetate; TEA; In dichloromethane;

DOI:10.1021/jm049248f

Reference yield:

2-α-(benzyloxycarbonyl)glycinyl)amino>benzophenone (108895-97-2) → (2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)carbamic acid tert-butyl ester (168162-29-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 7.0 g / NH₄OAc; AcOH / 12 h / 20 °C

2: Pd(OAc)2; TEA; triethylsilane / CH₂Cl₂ / 3 h / 20 °C

3: 3.78 g / CH₂Cl₂ / 2 h / 20 °C

With triethylsilane; palladium diacetate; TEA; ammonium acetate; acetic acid; In dichloromethane;

DOI:10.1021/jm049248f

Reference yield:

(2-aminophenyl)(phenyl)methanone (2835-77-0) → (2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)carbamic acid tert-butyl ester (168162-29-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: isobutyl chloroformate; N-methylmorpholine / CH₂Cl₂ / 0.5 h / Heating

1.2: 86 percent / CH₂Cl₂ / 0.5 h / Heating

2.1: NH₃(gas); mercuric chloride / tetrahydrofuran / 3 h / 0 - 20 °C

3.1: 7.0 g / NH₄OAc; AcOH / 12 h / 20 °C

4.1: Pd(OAc)2; TEA; triethylsilane / CH₂Cl₂ / 3 h / 20 °C

5.1: 3.78 g / CH₂Cl₂ / 2 h / 20 °C

With 4-methyl-morpholine; triethylsilane; palladium diacetate; TEA; ammonium acetate; ammonia; acetic acid; mercury dichloride; isobutyl chloroformate; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm049248f

upstream raw materials:

di-tert-butyl dicarbonate

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

benzyl 2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-ylcarbamate

2-α-(benzyloxycarbonyl)glycinyl)amino>benzophenone

Downstream raw materials:

3(S)-acetylamino-N-{1-[((3S)-2-benzyloxy-5-oxo-tetrahydrofuran-3-ylcarbamoyl)methyl]-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl}succinamic acid benzyl ester

{1-[((3S)-2-benzyloxy-5-oxo-tetrahydrofuran-3-ylcarbamoyl)methyl]-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl}carbamic acid tert-butyl ester

(3-tert-butoxycarbonylamino-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-1-yl)acetic acid

(3-tert-butoxycarbonylamino-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-1-yl)acetic acid ethyl ester