1-<1-(tert-Butoxycarbonyl)-3-<(tert-butoxycarbonyl)amino>propyl>-3-<(allyloxycarbonyl)amino>-6,7-bis(benzyloxy)tetrahydroquinolin-2-one

Base Information

• Chemical Name: 1-<1-(tert-Butoxycarbonyl)-3-<(tert-butoxycarbonyl)amino>propyl>-3-<(allyloxycarbonyl)amino>-6,7-bis(benzyloxy)tetrahydroquinolin-2-one
• CAS No.: 128218-07-5
• Molecular Formula: C₄₀H₄₉N₃O₉
• Molecular Weight: 715.844
• Mol file: 128218-07-5.mol

Synonyms:

Chemical Property of 1-<1-(tert-Butoxycarbonyl)-3-<(tert-butoxycarbonyl)amino>propyl>-3-<(allyloxycarbonyl)amino>-6,7-bis(benzyloxy)tetrahydroquinolin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-<1-(tert-Butoxycarbonyl)-3-<(tert-butoxycarbonyl)amino>propyl>-3-<(allyloxycarbonyl)amino>-6,7-bis(benzyloxy)tetrahydroquinolin-2-one

There total 20 articles about 1-<1-(tert-Butoxycarbonyl)-3-<(tert-butoxycarbonyl)amino>propyl>-3-<(allyloxycarbonyl)amino>-6,7-bis(benzyloxy)tetrahydroquinolin-2-one 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: 67.0%

di-tert-butyl dicarbonate (24424-99-5) + 2-(3-Allyloxycarbonylamino-6,7-bis-benzyloxy-2-oxo-3,4-dihydro-2H-quinolin-1-yl)-4-amino-butyric acid tert-butyl ester → 5--2,3-dihydro-8,9-bis(benzyloxy)-1H-pyrimido<1,2-a>quinoline-1-carboxylic acid tert-butyl ester (128218-09-7) + 1-<1-(tert-Butoxycarbonyl)-3-<(tert-butoxycarbonyl)amino>propyl>-3-<(allyloxycarbonyl)amino>-6,7-bis(benzyloxy)tetrahydroquinolin-2-one (128218-07-5,128218-08-6)

Guidance literature:

With sodium hydrogencarbonate; In water; ethyl acetate; overnight;

DOI:10.1021/jo00301a008

Reference yield:

tert-Butyl α-bromo-γ-N-phthalimidobutyrate (128217-88-9) → 1-<1-(tert-Butoxycarbonyl)-3-<(tert-butoxycarbonyl)amino>propyl>-3-<(allyloxycarbonyl)amino>-6,7-bis(benzyloxy)tetrahydroquinolin-2-one (128218-07-5,128218-08-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) NaH / 1.) THF, 30 min, 2.) reflux, 72 h

2: hydrazine hydrate / ethanol / 0.25 h / Heating

3: 95 percent / NaHCO₃ / ethyl acetate; H₂O / overnight

With sodium hydride; sodium hydrogencarbonate; hydrazine hydrate; In ethanol; water; ethyl acetate;

DOI:10.1021/jo00301a008

Reference yield:

3,4-dihydroxy-L-phenylalanine (59-92-7,90638-38-3) → 1-<1-(tert-Butoxycarbonyl)-3-<(tert-butoxycarbonyl)amino>propyl>-3-<(allyloxycarbonyl)amino>-6,7-bis(benzyloxy)tetrahydroquinolin-2-one (128218-07-5,128218-08-6)

Guidance literature:

Multi-step reaction with 8 steps

1: SOCl₂ / 48 h / Ambient temperature

2: NaHCO₃ / H₂O; tetrahydrofuran / overnight

3: K₂CO₃, NaI / ethanol / 4 h / Heating

4: 95 percent / nitric acid (d = 1.4) / acetic acid / 2 h / 0 °C

5: 68 percent / iron powder, glacial acetic acid / 3 h / 90 - 100 °C

6: 1.) NaH / 1.) THF, 30 min, 2.) reflux, 72 h

7: hydrazine hydrate / ethanol / 0.25 h / Heating

8: 95 percent / NaHCO₃ / ethyl acetate; H₂O / overnight

With thionyl chloride; nitric acid; iron; sodium hydride; sodium hydrogencarbonate; potassium carbonate; hydrazine hydrate; acetic acid; sodium iodide; In tetrahydrofuran; ethanol; water; acetic acid; ethyl acetate;

DOI:10.1021/jo00301a008

upstream raw materials:

di-tert-butyl dicarbonate

dopa

2-Amino-3-(3,4-bis-benzyloxy-phenyl)-propionic acid ethyl ester

3-(3,4-Bis-benzyloxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid ethyl ester

Downstream raw materials:

1-<1-(tert-Butoxycarbonyl)-3-<(tert-butoxycarbonyl)amino>propyl>-3-<(allyloxycarbonyl)amino>-6,7-bis(benzyloxy)tetrahydroquinoline-2-thione