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

HRID 1695363Notes

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].C[O:23][C:24]([C:26]1[NH:27]N=C(OCC2C(C3C=CC=CC=3)=NOC=2C)[CH:30]=1)=O.N[C@H](CO)C>>[OH:23][CH2:24][C@@H:26]([NH:27][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])[CH3:30]

Participants

Reactant 3

HCID 80307L-Alaninol

HCID 66643879HCID 66643879, compound

HCID 66643884HCID 66643884, compound

Product 1

HCID 595684325-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-2H-pyrazole-3-carboxylic acid ((S)-2-hydroxy-1-methyl-ethyl)-amideYield 6%

Procedure

As described for example 6, 5-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-2H-pyrazole-3-carboxylic acid methyl ester (100 mg, 0.34 mmol), instead of 5-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-2H-pyrazole-3-carboxylic acid methyl ester, was converted, using L-alaninol instead of ethanolamine, to the title compound (7 mg, 6%) which was obtained as a colorless oil. MS: m/e=337.4 [M+H]+.

Sources & evidence

ORD record: ord-468cfe23c5ad4f888f7e48f7fcdb0c9d
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163728B2

Reaction notes

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