Ethanolamine → 3-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid (2-hydroxy-ethyl)-amide

HRID 1920923Notes

Reaction equation

HRID 1920923 reaction equation
COC(C1ON=C(OC[C:12]2[C:13]([CH2:18]CCC)=[N:14]OC=2C)C=1)=O.CO[C:24]([C:26]1[O:30][N:29]=[C:28]([O:31][CH2:32][C:33]2[C:34]([C:39]3[CH:44]=[CH:43][CH:42]=CN=3)=[N:35][O:36][C:37]=2[CH3:38])[CH:27]=1)=[O:25].[CH2:45]([CH2:47][NH2:48])[OH:46]>>[CH:13]([NH2:14])([CH3:18])[CH3:12].[OH:46][CH2:45][CH2:47][NH:48][C:24]([C:26]1[O:30][N:29]=[C:28]([O:31][CH2:32][C:33]2[C:34]([CH2:39][CH2:44][CH2:43][CH3:42])=[N:35][O:36][C:37]=2[CH3:38])[CH:27]=1)=[O:25]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 67491973HCID 67491973, compoundHCID 674920483-(5-Methyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid methyl ester

Product 2

HCID 6363IsopropylamineHCID 594481273-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid (2-hydroxy-ethyl)-amideYield 47%

Procedure

As described for example 14e, 3-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid methyl ester (201 mg, 0.68 mmol), instead of 3-(5-methyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid methyl ester, was converted, using ethanolamine (50 mg, 0.82 mmol), instead of isopropyl amine, to the title compound (103 mg, 47%) which was obtained as a colourless gum after purification by chromatography (silica, heptane:ethyl acetate=1:1 to 0:1). MS: m/e=324.3 [M+H]+.

Sources & evidence

ORD record
ord-9ab344ac2a934bb78ee85d5171518231
Source dataset
uspto-grants-2012_05
Patent number
US08173652B2

Reaction notes

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