(1S,2S)-2-aminocyclopentan-1-ol hydrochloride → 2-[(e)-2-(3-Butyl-5-methyl-isoxazol-4-yl)-vinyl]-4-methyl-thiazole-5-carboxylic acid ((1s,2s)-2-hydroxy-cyclopentyl)-amide
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].[CH2:22]1[CH2:26][C@H:25]([OH:27])[C@@H:24]([NH2:28])[CH2:23]1.Cl>>[OH:27][C@H:25]1[CH2:26][CH2:22][CH2:23][C@@H:24]1[NH:28][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]Participants
3
Reactant 2
Product 1
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 trans-(1S,2S)-2-aminocyclopentanol hydrochloride instead of rac-2-amino-1-butanol, to the title compound (127 mg, 65%) which was obtained as an off white solid after purification by chromatography (silica, 50 to 100% ethyl acetate in heptane) and recrystallization from ethyl acetate/heptane. MS: m/e=390.3 [M+H]+.
Sources & evidence
- ORD record
- ord-dff3918f44354b539c4d67b66d1762ea
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08178522B2
Reaction notes
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