L-Alaninol → 3-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid ((S)-2-hydroxy-1-methyl-ethyl)-amide

HRID 1920925Notes

Reaction equation

CO[C:3]([C:5]1[O:9][N:8]=[C:7]([O:10][CH2:11][C:12]2[C:13]([CH2:18][CH2:19][CH2:20][CH3:21])=[N:14][O:15][C:16]=2[CH3:17])[CH:6]=1)=[O:4].[OH:22][CH2:23][C@@H:24]([NH2:26])[CH3:25]>>[CH2:23]([CH2:24][NH2:26])[OH:22].[OH:22][CH2:23][C@@H:24]([NH:26][C:3]([C:5]1[O:9][N:8]=[C:7]([O:10][CH2:11][C:12]2[C:13]([CH2:18][CH2:19][CH2:20][CH3:21])=[N:14][O:15][C:16]=2[CH3:17])[CH:6]=1)=[O:4])[CH3:25]

Participants

Reactant 2

HCID 80307L-Alaninol

HCID 67491973HCID 67491973, compound

Product 2

HCID 700Ethanolamine

HCID 594481283-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid ((S)-2-hydroxy-1-methyl-ethyl)-amideYield 108.3%

Procedure

As described for example 24b, 3-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid methyl ester (199 mg, 0.68 mmol), was converted using (S)-1-hydroxymethylethylamine (61 mg, 0.81 mmol), instead of ethanolamine, to the title compound (148 mg, 65%) which was obtained as a colourless gum after purification by chromatography (silica, heptane:ethyl acetate=1:1 to 0:1). MS: m/e=338.4 [M+H]+.

Sources & evidence

ORD record: ord-5287838deba34150b143b4d99f4a7a93
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173652B2

Reaction notes

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