Technology Process of (2S,3R)-2-(biphenyl-4-ylmethoxy)-N,3-dihydroxy-3-isoxazol-5-yl-2-methylpropanamide
There total 6 articles about (2S,3R)-2-(biphenyl-4-ylmethoxy)-N,3-dihydroxy-3-isoxazol-5-yl-2-methylpropanamide 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:
- Guidance literature:
-
(4S)-3-[(2S,3S)-2-(biphenyl-4-ylmethoxy)-3-hydroxy-2-methyl-3-(isoxazol-5-yl)propanoyl]-5,5-dimethyl-4-phenyl-1,3-oxazolidin-2-one;
With
methanol; methylmagnesium bromide; hydroxylamine hydrochloride;
at 25 ℃;
for 2h;
Inert atmosphere;
With
water;
In
methanol;
pH=7;
Sodium phosphate buffer;
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide; mineral oil / 2 h / -20 - 50 °C / Inert atmosphere
2.1: water; lithium hydroxide / tetrahydrofuran / 18 h / 25 °C / Inert atmosphere
3.1: thionyl chloride / 1 h / 65 °C / Inert atmosphere
4.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere
4.2: 3.5 h / -78 - 25 °C / Inert atmosphere
5.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 0.5 h / -78 °C / Inert atmosphere
5.2: 1 h / -40 °C / Inert atmosphere
5.3: 2 h / -78 - -40 °C / Inert atmosphere
6.1: hydroxylamine hydrochloride; lithium methanolate / methanol / 5 h / 25 °C / Inert atmosphere
With
n-butyllithium; thionyl chloride; hydroxylamine hydrochloride; lithium methanolate; water; sodium hydride; lithium hydroxide; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; hexane; n-heptane; ethylbenzene; N,N-dimethyl-formamide; mineral oil;
DOI:10.1016/j.bmcl.2012.01.140
- 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
![(4S)-3-[(2S,3S)-2-(biphenyl-4-ylmethoxy)-3-hydroxy-2-methyl-3-(isoxazol-5-yl)propanoyl]-5,5-dimethyl-4-phenyl-1,3-oxazolidin-2-one](/Databaselist/images/loading.webp)
