(S)-methyl 2-(5-(bis(tert-butoxycarbonyl)amino)-2-cyanophenylamino)-4-methylpentanoate

Base Information

• Chemical Name: (S)-methyl 2-(5-(bis(tert-butoxycarbonyl)amino)-2-cyanophenylamino)-4-methylpentanoate
• CAS No.: 1425822-16-7
• Molecular Formula: C₂₄H₃₅N₃O₆
• Molecular Weight: 461.558
• Mol file: 1425822-16-7.mol

Synonyms:(S)-methyl 2-(5-(bis(tert-butoxycarbonyl)amino)-2-cyanophenylamino)-4-methylpentanoate

Chemical Property of (S)-methyl 2-(5-(bis(tert-butoxycarbonyl)amino)-2-cyanophenylamino)-4-methylpentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-methyl 2-(5-(bis(tert-butoxycarbonyl)amino)-2-cyanophenylamino)-4-methylpentanoate

There total 4 articles about (S)-methyl 2-(5-(bis(tert-butoxycarbonyl)amino)-2-cyanophenylamino)-4-methylpentanoate 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: 93.0%

N-(3-bromo-4-cyanophenyl)imidodicarbonic acid bis(1,1-dimethylethyl) ester (1425822-14-5) + methyl (L)-leucinate hydrochloride (7517-19-3) → (S)-methyl 2-(5-(bis(tert-butoxycarbonyl)amino)-2-cyanophenylamino)-4-methylpentanoate (1425822-16-7)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In toluene; at 110 ℃; for 4h; Inert atmosphere;

DOI:10.1016/j.bmc.2012.11.042

Reference yield:

2-bromo-4-fluorobenzonitrile (36282-26-5) → (S)-methyl 2-(5-(bis(tert-butoxycarbonyl)amino)-2-cyanophenylamino)-4-methylpentanoate (1425822-16-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 5 h / 140 °C

2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / water; dichloromethane / 3.5 h / 20 °C

3: dmap; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / 0 °C / Reflux

4: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / toluene / 4 h / 110 °C / Inert atmosphere

With dmap; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; toluene;

DOI:10.1016/j.bmc.2012.11.042

Reference yield:

4-amino-2-bromobenzonitrile (53312-82-6) → (S)-methyl 2-(5-(bis(tert-butoxycarbonyl)amino)-2-cyanophenylamino)-4-methylpentanoate (1425822-16-7)

Guidance literature:

Multi-step reaction with 2 steps

1: dmap; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / 0 °C / Reflux

2: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / toluene / 4 h / 110 °C / Inert atmosphere

With dmap; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; toluene;

DOI:10.1016/j.bmc.2012.11.042

upstream raw materials:

N-(3-bromo-4-cyanophenyl)imidodicarbonic acid bis(1,1-dimethylethyl) ester

methyl (L)-leucinate hydrochloride

2-bromo-4-fluorobenzonitrile

2-bromo-4-(4-methoxybenzylamino)benzonitrile

Downstream raw materials:

C₂₄H₃₃N₃O

C₂₇H₃₇N₃O₃

C₂₅H₃₃N₃O₃

(S)-ethyl 4-[8-amino-1,2,4,5-tetrahydro-2-(2-methylpropyl)-4-(3-methylbutyl)-3-oxo-3H-1,4-benzodiazepin-7-yl]-3-[2-(benzyloxy)ethoxy]benzoate