1-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-6-yl)pyrrole-2-carboxylic acid 4-methoxybenzylamide

Base Information

• Chemical Name: 1-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-6-yl)pyrrole-2-carboxylic acid 4-methoxybenzylamide
• CAS No.: 1615684-98-4
• Molecular Formula: C₂₀H₁₉BN₂O₄
• Molecular Weight: 362.193

Synonyms:1-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-6-yl)pyrrole-2-carboxylic acid 4-methoxybenzylamide

Chemical Property of 1-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-6-yl)pyrrole-2-carboxylic acid 4-methoxybenzylamide

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Technology Process of 1-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-6-yl)pyrrole-2-carboxylic acid 4-methoxybenzylamide

There total 10 articles about 1-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-6-yl)pyrrole-2-carboxylic acid 4-methoxybenzylamide 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: 44.4%

1-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)-1H-pyrrole-2-carboxylic acid (1615684-94-0) + 4-methoxy-benzylamine (2393-23-9) → 1-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-6-yl)pyrrole-2-carboxylic acid 4-methoxybenzylamide (1615684-98-4)

Guidance literature:

1-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)-1H-pyrrole-2-carboxylic acid; With benzotriazol-1-ol; 1,2-dichloro-ethane; In dichloromethane; at 0 - 20 ℃; for 0.5h;

4-methoxy-benzylamine; In dichloromethane;

DOI:10.1016/j.ejmech.2014.04.079

Reference yield:

2-bromo-4-nitrobenzoyl chloride (856794-72-4) → 1-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-6-yl)pyrrole-2-carboxylic acid 4-methoxybenzylamide (1615684-98-4)

Guidance literature:

Multi-step reaction with 9 steps

1.1: triethylamine / 1 h / 0 - 20 °C

2.1: tin(II) chloride dihdyrate / ethyl acetate / 4 h / Reflux

3.1: ethyl acetate / 4 h / Reflux

4.1: lithium borohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

5.1: n-butyllithium / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere

5.2: 20 °C / Inert atmosphere

6.1: hydrogenchloride / water; tetrahydrofuran / Inert atmosphere

7.1: trichlorophosphate / 0.25 h / 0 - 20 °C / Inert atmosphere

7.2: 1.25 h / 0 °C / Inert atmosphere

8.1: silver nitrate; sodium hydroxide / water / 0 - 20 °C / Inert atmosphere

9.1: 1,2-dichloro-ethane; benzotriazol-1-ol / dichloromethane / 0.5 h / 0 - 20 °C

With hydrogenchloride; lithium borohydride; n-butyllithium; tin(II) chloride dihdyrate; benzotriazol-1-ol; silver nitrate; 1,2-dichloro-ethane; triethylamine; sodium hydroxide; trichlorophosphate; In tetrahydrofuran; dichloromethane; water; ethyl acetate;

DOI:10.1016/j.ejmech.2014.04.079

Reference yield:

C17H24BNO3 → 1-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-6-yl)pyrrole-2-carboxylic acid 4-methoxybenzylamide (1615684-98-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: hydrogenchloride / water; tetrahydrofuran / Inert atmosphere

2.1: trichlorophosphate / 0.25 h / 0 - 20 °C / Inert atmosphere

2.2: 1.25 h / 0 °C / Inert atmosphere

3.1: silver nitrate; sodium hydroxide / water / 0 - 20 °C / Inert atmosphere

4.1: 1,2-dichloro-ethane; benzotriazol-1-ol / dichloromethane / 0.5 h / 0 - 20 °C

With hydrogenchloride; benzotriazol-1-ol; silver nitrate; 1,2-dichloro-ethane; sodium hydroxide; trichlorophosphate; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/j.ejmech.2014.04.079

upstream raw materials:

1-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)-1H-pyrrole-2-carboxylic acid

4-methoxy-benzylamine

2-bromo-4-nitrobenzoyl chloride

2-bromo-4-nitrotoluene

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