2-Amino-1-butanol, (-)- → 2-[(E)-2-(3-Butyl-5-methyl-isoxazol-4-yl)-vinyl]-4-methyl-thiazole-5-carboxylic acid ((R)-1-hydroxymethyl-propyl)-amide

HRID 1923620Notes

Reaction equation

HRID 1923620 reaction equation
[CH2:1]([C:5]1[C:9](/[CH:10]=[CH:11]/[C:12]2[S:13][C:14]([C:18]([OH:20])=O)=[C:15]([CH3:17])[N:16]=2)=[C:8]([CH3:21])[O:7][N:6]=1)[CH2:2][CH2:3][CH3:4].[NH2:22][C@H:23]([CH2:26][CH3:27])[CH2:24][OH:25]>>[OH:25][CH2:24][C@H:23]([NH:22][C:18]([C:14]1[S:13][C:12](/[CH:11]=[CH:10]/[C:9]2[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[N:6][O:7][C:8]=2[CH3:21])=[N:16][C:15]=1[CH3:17])=[O:20])[CH2:26][CH3:27]

Participants

3

Reactant 2

HCID 27238562-Amino-1-butanol, (-)-HCID 595685392-[(E)-2-(3-Butyl-5-methyl-isoxazol-4-yl)-vinyl]-4-methyl-thiazole-5-carboxylic acid

Product 1

HCID 497813662-[(E)-2-(3-Butyl-5-methyl-isoxazol-4-yl)-vinyl]-4-methyl-thiazole-5-carboxylic acid ((R)-1-hydroxymethyl-propyl)-amideYield 80%

Procedure

As described for example 104, 2-[(E)-2-(3-butyl-5-methyl-isoxazol-4-yl)-vinyl]-4-methyl-thiazole-5-carboxylic acid (153 mg, 0.5 mmol) was converted, using (R)-2-amino-1-butanol instead of rac-2-amino-1-butanol, to the title compound (151 mg, 80%) which was obtained as a light yellow solid after purification by chromatography (silica, 50 to 100% ethyl acetate in heptane) and recrystallization from ethyl acetate/heptane. MS: m/e=378.3 [M+H]+.

Sources & evidence

ORD record
ord-65373c1ade0b4de7af92e63038ce7474
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

Loading…