(R)-1-{2-[4-(benzylamino)-2-oxopyridin-1(2H)-yl]acetamido}-3-methylbutylboronic acid pinanediol ester

Base Information

• Chemical Name: (R)-1-{2-[4-(benzylamino)-2-oxopyridin-1(2H)-yl]acetamido}-3-methylbutylboronic acid pinanediol ester
• CAS No.: 1624283-91-5
• Molecular Formula: C₂₉H₄₀BN₃O₄
• Molecular Weight: 505.465
• Mol file: 1624283-91-5.mol

Synonyms:(R)-1-{2-[4-(benzylamino)-2-oxopyridin-1(2H)-yl]acetamido}-3-methylbutylboronic acid pinanediol ester

Chemical Property of (R)-1-{2-[4-(benzylamino)-2-oxopyridin-1(2H)-yl]acetamido}-3-methylbutylboronic acid pinanediol ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-1-{2-[4-(benzylamino)-2-oxopyridin-1(2H)-yl]acetamido}-3-methylbutylboronic acid pinanediol ester

There total 6 articles about (R)-1-{2-[4-(benzylamino)-2-oxopyridin-1(2H)-yl]acetamido}-3-methylbutylboronic acid pinanediol ester 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: 70.0%

(aR,3aS,4S,6S,7aR)-hexahydro-3a,8,8-trimethyl-α-(2-methylpropyl)-4,6-methano-1,3,2-benzodioxaborole-2-methanamine 2,2,2-trifluoroacetate (1310383-72-2,179324-87-9) + 2-[4-(benzylamino)-2-oxopyridin-1(2H)-yl]acetic acid (1624283-78-8) → (R)-1-{2-[4-(benzylamino)-2-oxopyridin-1(2H)-yl]acetamido}-3-methylbutylboronic acid pinanediol ester (1624283-91-5)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -15 - 20 ℃; for 3h;

DOI:10.1002/cmdc.201402075

Reference yield:

ethyl 2-[4-(benzylamino)-2-oxopyridin-1(2H)-yl]acetate (1624283-65-3) → (R)-1-{2-[4-(benzylamino)-2-oxopyridin-1(2H)-yl]acetamido}-3-methylbutylboronic acid pinanediol ester (1624283-91-5)

Guidance literature:

Multi-step reaction with 2 steps

1: lithium hydroxide / ethanol; water / 4 h / 0 - 20 °C

2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / -15 - 20 °C

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; lithium hydroxide; In ethanol; dichloromethane; water;

DOI:10.1002/cmdc.201402075

Reference yield:

N-benzyl-2-(benzyloxy)pyridin-4-amine (1624283-59-5) → (R)-1-{2-[4-(benzylamino)-2-oxopyridin-1(2H)-yl]acetamido}-3-methylbutylboronic acid pinanediol ester (1624283-91-5)

Guidance literature:

Multi-step reaction with 4 steps

1: palladium 10% on activated carbon; hydrogen / methanol; ethyl acetate / 2 h / 20 °C

2: sodium hydride / N,N-dimethyl-formamide / 3 h / 0 - 20 °C

3: lithium hydroxide / ethanol; water / 4 h / 0 - 20 °C

4: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / -15 - 20 °C

With palladium 10% on activated carbon; hydrogen; sodium hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; lithium hydroxide; In methanol; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1002/cmdc.201402075

upstream raw materials:

(aR,3aS,4S,6S,7aR)-hexahydro-3a,8,8-trimethyl-α-(2-methylpropyl)-4,6-methano-1,3,2-benzodioxaborole-2-methanamine 2,2,2-trifluoroacetate

2-[4-(benzylamino)-2-oxopyridin-1(2H)-yl]acetic acid

ethyl 2-[4-(benzylamino)-2-oxopyridin-1(2H)-yl]acetate

N-benzyl-2-(benzyloxy)pyridin-4-amine

Downstream raw materials:

(R)-1-{2-[4-(benzylamino)-2-oxopyridin-1(2H)-yl]acetamido}-3-methylbutylboronic acid