(2R)-3-{2-[(2-amino-pyridin-4-ylacetyl)-amino]-2-borono-ethyl}-2-hydroxy-benzoic acid

Base Information

Chemical Name:(2R)-3-{2-[(2-amino-pyridin-4-ylacetyl)-amino]-2-borono-ethyl}-2-hydroxy-benzoic acid
CAS No.:1256336-19-2
Molecular Formula:C₁₆H₁₈BN₃O₆
Molecular Weight:359.146
Hs Code.:

Synonyms:(2R)-3-{2-[(2-amino-pyridin-4-ylacetyl)-amino]-2-borono-ethyl}-2-hydroxy-benzoic acid

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Chemical Property of (2R)-3-{2-[(2-amino-pyridin-4-ylacetyl)-amino]-2-borono-ethyl}-2-hydroxy-benzoic acid

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Technology Process of (2R)-3-{2-[(2-amino-pyridin-4-ylacetyl)-amino]-2-borono-ethyl}-2-hydroxy-benzoic acid

There total 9 articles about (2R)-3-{2-[(2-amino-pyridin-4-ylacetyl)-amino]-2-borono-ethyl}-2-hydroxy-benzoic acid 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:

: 1256337-00-4
3-(2-((2-tert-butoxycarbonylamino-pyridin-4-ylacetyl)-amino)-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0(2,6)]dec-4-yl)-ethyl)-2-methoxy-benzoic acid tert-butyl ester

: 1256336-19-2
(2R)-3-{2-[(2-amino-pyridin-4-ylacetyl)-amino]-2-borono-ethyl}-2-hydroxy-benzoic acid

Guidance literature:: 3-(2-((2-tert-butoxycarbonylamino-pyridin-4-ylacetyl)-amino)-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0(2,6)]dec-4-yl)-ethyl)-2-methoxy-benzoic acid tert-butyl ester; With boron trichloride; In dichloromethane; at -78 ℃; Inert atmosphere;

With water; In dichloromethane; at 0 ℃; Inert atmosphere;

Reference yield:

: 3678-62-4
2-chloro-4-picoline

: 1256336-19-2
(2R)-3-{2-[(2-amino-pyridin-4-ylacetyl)-amino]-2-borono-ethyl}-2-hydroxy-benzoic acid

Guidance literature:: Multi-step reaction with 5 steps

1.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 2 h / -78 °C

1.2: -78 - 20 °C

2.1: caesium carbonate / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / tetrahydrofuran / 20 h / Inert atmosphere; Heating; Reflux

3.1: methanol; water; sodium hydroxide / 1.5 h / Reflux

3.2: pH 4 - 5

4.1: 4-methyl-morpholine; 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 1 h / 0 °C

4.2: 0 - 20 °C

5.1: boron trichloride / dichloromethane / -78 °C / Inert atmosphere

5.2: 0 °C / Inert atmosphere

With 4-methyl-morpholine; methanol; 1-hydroxy-pyrrolidine-2,5-dione; water; boron trichloride; caesium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; lithium diisopropyl amide; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; hexane; dichloromethane;

Reference yield:

: 937236-73-2
ethyl 2-(2-chloropyridin-4-yl)acetate

: 1256336-19-2
(2R)-3-{2-[(2-amino-pyridin-4-ylacetyl)-amino]-2-borono-ethyl}-2-hydroxy-benzoic acid

Guidance literature:: Multi-step reaction with 4 steps

1.1: caesium carbonate / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / tetrahydrofuran / 20 h / Inert atmosphere; Heating; Reflux

2.1: methanol; water; sodium hydroxide / 1.5 h / Reflux

2.2: pH 4 - 5

3.1: 4-methyl-morpholine; 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 1 h / 0 °C

3.2: 0 - 20 °C

4.1: boron trichloride / dichloromethane / -78 °C / Inert atmosphere

4.2: 0 °C / Inert atmosphere

With 4-methyl-morpholine; methanol; 1-hydroxy-pyrrolidine-2,5-dione; water; boron trichloride; caesium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; dichloromethane;