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

HRID 1695365Notes

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][CH:23]([CH2:26][OH:27])[CH2:24][OH:25]>>[OH:25][CH2:24][CH: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])[CH2:26][OH:27]

Participants

Reactant 2

HCID 68294Serinol

HCID 66643879HCID 66643879, compound

Product 1

HCID 595684295-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-2H-pyrazole-3-carboxylic acid (2-hydroxy-1-hydroxymethyl-ethyl)-amideYield 10%

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 2-amino-1,3-propandiol instead of L-alaninol, to the title compound (12 mg, 10%) which was obtained as a white solid. MS: m/e=353.3 [M+H]+.

Sources & evidence

ORD record: ord-458e54107d074c6594877a0eae530391
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163728B2

Reaction notes

Loading…