methyl (R,S)-8-[[[4-[N-(t-butoxycarbonyl)aminoiminomethyl]phenyl]amino]carbonyl]-2,3,4,5-tetrahydro-4-(2-phenylethyl)-1H-1,4-benzodiazepine-2-acetate

Base Information

• Chemical Name: methyl (R,S)-8-[[[4-[N-(t-butoxycarbonyl)aminoiminomethyl]phenyl]amino]carbonyl]-2,3,4,5-tetrahydro-4-(2-phenylethyl)-1H-1,4-benzodiazepine-2-acetate
• CAS No.: 165529-17-9
• Molecular Formula: C₃₃H₃₉N₅O₅
• Molecular Weight: 585.703
• Mol file: 165529-17-9.mol

Synonyms:methyl (R,S)-8-[[[4-[N-(t-butoxycarbonyl)aminoiminomethyl]phenyl]amino]carbonyl]-2,3,4,5-tetrahydro-4-(2-phenylethyl)-1H-1,4-benzodiazepine-2-acetate

Chemical Property of methyl (R,S)-8-[[[4-[N-(t-butoxycarbonyl)aminoiminomethyl]phenyl]amino]carbonyl]-2,3,4,5-tetrahydro-4-(2-phenylethyl)-1H-1,4-benzodiazepine-2-acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (R,S)-8-[[[4-[N-(t-butoxycarbonyl)aminoiminomethyl]phenyl]amino]carbonyl]-2,3,4,5-tetrahydro-4-(2-phenylethyl)-1H-1,4-benzodiazepine-2-acetate

There total 10 articles about methyl (R,S)-8-[[[4-[N-(t-butoxycarbonyl)aminoiminomethyl]phenyl]amino]carbonyl]-2,3,4,5-tetrahydro-4-(2-phenylethyl)-1H-1,4-benzodiazepine-2-acetate 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: 80.0%

tert-butyl [(4-aminophenyl)(imino)methyl]carbamate (147291-56-3) + methyl (R,S)-8-carboxy-2,3,4,5-tetrahydro-4-(2-phenylethyl)-1H-1,4-benzodiazepine-2-acetate (165529-16-8) → methyl (R,S)-8-[[[4-[N-(t-butoxycarbonyl)aminoiminomethyl]phenyl]amino]carbonyl]-2,3,4,5-tetrahydro-4-(2-phenylethyl)-1H-1,4-benzodiazepine-2-acetate (165529-17-9)

Guidance literature:

With pyridine; thionyl chloride; In dichloromethane;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → methyl (R,S)-8-[[[4-[N-(t-butoxycarbonyl)aminoiminomethyl]phenyl]amino]carbonyl]-2,3,4,5-tetrahydro-4-(2-phenylethyl)-1H-1,4-benzodiazepine-2-acetate (165529-17-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 56 percent / 1N aq. NaOH / tetrahydrofuran / 5 h

2: pyridine / 4 h / Ambient temperature

With pyridine; sodium hydroxide; In tetrahydrofuran;

DOI:10.1021/jm980166z

Reference yield:

2-nitro-4-(tert-butoxycarbonyl)benzyl bromide (65276-90-6) → methyl (R,S)-8-[[[4-[N-(t-butoxycarbonyl)aminoiminomethyl]phenyl]amino]carbonyl]-2,3,4,5-tetrahydro-4-(2-phenylethyl)-1H-1,4-benzodiazepine-2-acetate (165529-17-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 88 percent / Et₃N / tetrahydrofuran / 16 h / Ambient temperature

2: Fe, AcOH / ethanol / 16 h / Ambient temperature

3: methanol / 72 h / Heating

4: TFA / CH₂Cl₂ / 0.75 h / Ambient temperature

5: SOCl₂ / 0.25 h / Heating

6: pyridine / 4 h / Ambient temperature

With pyridine; thionyl chloride; iron; acetic acid; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane;

DOI:10.1021/jm980166z

upstream raw materials:

tert-butyl [(4-aminophenyl)(imino)methyl]carbamate

di-tert-butyl dicarbonate

2-nitro-4-(tert-butoxycarbonyl)benzyl bromide

4-aminobenzamidine dihydrochloride

Downstream raw materials:

[8-(4-carbamimidoyl-phenylcarbamoyl)-4-phenethyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-2-yl]-acetic acid methyl ester