tert-butyl (2S)-1-(methyl(1-phenylallyl)amino)-1-oxopent-4-en-2-ylcarbamate

Base Information

• Chemical Name: tert-butyl (2S)-1-(methyl(1-phenylallyl)amino)-1-oxopent-4-en-2-ylcarbamate
• CAS No.: 762289-11-2
• Molecular Formula: C₂₀H₂₈N₂O₃
• Molecular Weight: 344.454
• Mol file: 762289-11-2.mol

Synonyms:tert-butyl (2S)-1-(methyl(1-phenylallyl)amino)-1-oxopent-4-en-2-ylcarbamate

Chemical Property of tert-butyl (2S)-1-(methyl(1-phenylallyl)amino)-1-oxopent-4-en-2-ylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (2S)-1-(methyl(1-phenylallyl)amino)-1-oxopent-4-en-2-ylcarbamate

There total 2 articles about tert-butyl (2S)-1-(methyl(1-phenylallyl)amino)-1-oxopent-4-en-2-ylcarbamate 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: 60.0%

N-methyl-N-<α-phenyl-allyl>amine (86766-70-3) + (2S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoic acid (90600-20-7) → tert-butyl (2S)-1-(methyl(1-phenylallyl)amino)-1-oxopent-4-en-2-ylcarbamate (762289-11-2)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 4-N,N-dimethylaminopyridine trifluoroacetate; In dichloromethane; at -20 - 20 ℃;

Reference yield:

(Z)-N-methyl-1-phenylmethanimine (29086-12-2) → tert-butyl (2S)-1-(methyl(1-phenylallyl)amino)-1-oxopent-4-en-2-ylcarbamate (762289-11-2)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 0 - 20 °C / Inert atmosphere

2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 16 h / 20 °C / Inert atmosphere

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane; 1: |Grignard Reaction;

DOI:10.1016/j.bmcl.2015.05.061

Reference yield: 50.7%

tert-butyl (2S)-1-(methyl(1-phenylallyl)amino)-1-oxopent-4-en-2-ylcarbamate (762289-11-2) → tert-butyl (3S,7R,Z)-1-methyl-2-oxo-7-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-ylcarbamate (762289-15-6) + tert-butyl (3S,7S,Z)-1-methyl-2-oxo-7-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-ylcarbamate

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In toluene; at 80 ℃; for 2h; Inert atmosphere;

DOI:10.1016/j.bmcl.2015.05.061

upstream raw materials:

N-methyl-N-<α-phenyl-allyl>amine

(2S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoic acid

(Z)-N-methyl-1-phenylmethanimine

Downstream raw materials:

tert-butyl (3S,7R,Z)-1-methyl-2-oxo-7-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-ylcarbamate

tert-butyl[(3S,7S)-1-methyl-2-oxo-7-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-yl]carbamate

(3S,7R,Z)-3-amino-1-methyl-7-phenyl-3,4-dihydro-1H-azepin-2(7H)-one