(2S,3S)-2-(biphenyl-4-ylmethoxy)-N,3-dihydroxy-2-methyl-3-pyridin-3-ylpropanamide

Base Information

Chemical Name:(2S,3S)-2-(biphenyl-4-ylmethoxy)-N,3-dihydroxy-2-methyl-3-pyridin-3-ylpropanamide
CAS No.:1219003-73-2
Molecular Formula:C₂₂H₂₂N₂O₄
Molecular Weight:378.428
Hs Code.:

Synonyms:(2S,3S)-2-(biphenyl-4-ylmethoxy)-N,3-dihydroxy-2-methyl-3-pyridin-3-ylpropanamide

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S,3S)-2-(biphenyl-4-ylmethoxy)-N,3-dihydroxy-2-methyl-3-pyridin-3-ylpropanamide

Chemical Property:

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Technology Process of (2S,3S)-2-(biphenyl-4-ylmethoxy)-N,3-dihydroxy-2-methyl-3-pyridin-3-ylpropanamide

There total 6 articles about (2S,3S)-2-(biphenyl-4-ylmethoxy)-N,3-dihydroxy-2-methyl-3-pyridin-3-ylpropanamide 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: 15.0%

: 1219003-73-2
(2S,3S)-2-(biphenyl-4-ylmethoxy)-N,3-dihydroxy-2-methyl-3-pyridin-3-ylpropanamide

Guidance literature:

Reference yield:

: 1219004-71-3
(4S)-3-[(2S,3S)-2-(biphenyl-4-ylmethoxy)-3-hydroxy-2-methyl-3-(pyridin-3-yl)propanoyl]-5,5-dimethyl-4-phenyl-1,3-oxazolidin-2-one

: 1219003-73-2
(2S,3S)-2-(biphenyl-4-ylmethoxy)-N,3-dihydroxy-2-methyl-3-pyridin-3-ylpropanamide

Guidance literature:: With hydroxylamine hydrochloride; lithium methanolate; In methanol; at 25 ℃; for 5h; Inert atmosphere;
DOI:10.1016/j.bmcl.2012.01.140

Reference yield:

: 1219004-57-5
methyl (2S)-2-(biphenyl-4-ylmethoxy)propanoate

: 1219003-73-2
(2S,3S)-2-(biphenyl-4-ylmethoxy)-N,3-dihydroxy-2-methyl-3-pyridin-3-ylpropanamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: water; lithium hydroxide / tetrahydrofuran / 18 h / 25 °C / Inert atmosphere

2.1: thionyl chloride / 1 h / 65 °C / Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

3.2: 3.5 h / -78 - 25 °C / Inert atmosphere

4.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 0.5 h / -78 °C / Inert atmosphere

4.2: 1 h / -40 °C / Inert atmosphere

4.3: 2 h / -78 - -40 °C / Inert atmosphere

5.1: hydroxylamine hydrochloride; lithium methanolate / methanol / 5 h / 25 °C / Inert atmosphere

With n-butyllithium; thionyl chloride; hydroxylamine hydrochloride; lithium methanolate; water; lithium hydroxide; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; n-heptane; ethylbenzene;
DOI:10.1016/j.bmcl.2012.01.140