Benzyl 2-{[2,6-bis(N-tert-butoxycarbonyl-L-phenylalanylamino)-4-pyridyl]oxy} acetate

Base Information

• Chemical Name: Benzyl 2-{[2,6-bis(N-tert-butoxycarbonyl-L-phenylalanylamino)-4-pyridyl]oxy} acetate
• CAS No.: 350697-56-2
• Molecular Formula: C₄₂H₄₉N₅O₉
• Molecular Weight: 767.879
• Mol file: 350697-56-2.mol

Synonyms:Benzyl 2-{[2,6-bis(N-tert-butoxycarbonyl-L-phenylalanylamino)-4-pyridyl]oxy} acetate

Chemical Property of Benzyl 2-{[2,6-bis(N-tert-butoxycarbonyl-L-phenylalanylamino)-4-pyridyl]oxy} acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzyl 2-{[2,6-bis(N-tert-butoxycarbonyl-L-phenylalanylamino)-4-pyridyl]oxy} acetate

There total 7 articles about Benzyl 2-{[2,6-bis(N-tert-butoxycarbonyl-L-phenylalanylamino)-4-pyridyl]oxy} 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: 75.0%

{1-[6-(2-tert-butoxycarbonylamino-3-phenyl-propionylamino)-4-hydroxy-pyridin-2-ylcarbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester (350697-55-1) + Benzyl bromoacetate (5437-45-6) → Benzyl 2-{[2,6-bis(N-tert-butoxycarbonyl-L-phenylalanylamino)-4-pyridyl]oxy} acetate (350697-56-2)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 15h;

DOI:10.1002/1521-3765(20010504)7:9<1889::AID-CHEM1889>3.0.CO;2-7

Reference yield:

4-Benzyloxy-2,6-bis(N-tert-butoxycarbonyl-L-phenylalaninylamino)pyridine (244089-24-5) → Benzyl 2-{[2,6-bis(N-tert-butoxycarbonyl-L-phenylalanylamino)-4-pyridyl]oxy} acetate (350697-56-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / ammonium formate / 10percent Pd/C / methanol / 0.5 h / Heating

2: 75 percent / K₂CO₃ / dimethylformamide / 15 h / 20 °C

With ammonium formate; potassium carbonate; 10percent Pd/C; In methanol; N,N-dimethyl-formamide;

DOI:10.1002/1521-3765(20010504)7:9<1889::AID-CHEM1889>3.0.CO;2-7

Reference yield:

4?benzyloxy?2,6?diaminopyridine (18986-54-4) → Benzyl 2-{[2,6-bis(N-tert-butoxycarbonyl-L-phenylalanylamino)-4-pyridyl]oxy} acetate (350697-56-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 91 percent / 4-DMAP / CH₂Cl₂ / 24 h / 20 °C

2.1: 99 percent / H₂ / 10percent Pd/C / ethanol; CH₂Cl₂ / 18 h / 20 °C

3.1: 99 percent / K₂CO₃; TBAB / dimethylsulfoxide / 18 h / 20 °C

4.1: aq. TFA / CH₂Cl₂

5.1: N,O-bis(trimethylsilylacetamide) / acetonitrile / 2 h / 20 °C

5.2: TBAF / acetonitrile / 12 h / 20 °C

6.1: 94 percent / ammonium formate / 10percent Pd/C / methanol / 0.5 h / Heating

7.1: 75 percent / K₂CO₃ / dimethylformamide / 15 h / 20 °C

With dmap; N,O-bis-(trimethylsilyl)-acetamide; tetrabutylammomium bromide; hydrogen; ammonium formate; potassium carbonate; trifluoroacetic acid; 10percent Pd/C; In methanol; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/1521-3765(20010504)7:9<1889::AID-CHEM1889>3.0.CO;2-7

upstream raw materials:

{1-[6-(2-tert-butoxycarbonylamino-3-phenyl-propionylamino)-4-hydroxy-pyridin-2-ylcarbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester

Benzyl bromoacetate

4?benzyloxy?2,6?diaminopyridine

4-Benzyloxy-2,6-bis(N-tert-butoxycarbonyl-L-phenylalaninylamino)pyridine

Downstream raw materials:

2-[2,6-Bis(N-tert-butoxycarbonyl-L-phenylalanylamino)-4-pyridyloxy] acetic acid

2-{2,6-Bis[N-(9-fluorenylmethoxycarbonyl)-L-phenylalanyl]-4-pyridyloxy} acetic acid

{2,6-bis-[2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-pyridin-4-yloxy}-acetic acid benzyl ester

[2,6-Bis-((S)-2-amino-3-phenyl-propionylamino)-pyridin-4-yloxy]-acetic acid benzyl ester