(R)-(-)-2-Amino-1-propanol → 5-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-2H-pyrazole-3-carboxylic acid ((R)-2-hydroxy-1-methyl-ethyl)-amide

HRID 1695366Notes

Reaction equation

HRID 1695366 reaction equation
CO[C:3]([C:5]1[NH:6][N:7]=[C:8]([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:9]=1)=[O:4].[NH2:22][C@@H:23]([CH2:25][OH:26])[CH3:24]>>[OH:26][CH2:25][C@H:23]([NH:22][C:3]([C:5]1[NH:6][N:7]=[C:8]([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:9]=1)=[O:4])[CH3:24]

Participants

3

Reactant 2

HCID 80308(R)-(-)-2-Amino-1-propanolHCID 66643879HCID 66643879, compound

Product 1

HCID 666438335-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-2H-pyrazole-3-carboxylic acid ((R)-2-hydroxy-1-methyl-ethyl)-amideYield 90%

Procedure

As described for example 27, 5-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-2H-pyrazole-3-carboxylic acid methyl ester (100 mg, 0.34 mmol) was converted, using D-alaninol instead of L-alaninol, to the title compound (103 mg, 90%) which was obtained as a colorless oil.

Sources & evidence

ORD record
ord-5a831134f0f5446492a54ed8f76eccc2
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

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