L-Alaninol → 5-[3-(4-Chloro-phenyl)-isoxazol-4-ylmethoxy]-pyrazine-2-carboxylic acid ((R)-2-hydroxy-1-methyl-ethyl)-amide

HRID 600500Notes

Reaction equation

HRID 600500 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH2:13][O:14][C:15]3[N:16]=[CH:17][C:18]([C:21]([OH:23])=O)=[N:19][CH:20]=3)=[CH:11][O:10][N:9]=2)=[CH:4][CH:3]=1.[NH2:24][C@H:25]([CH2:27][OH:28])[CH3:26]>>[OH:28][CH2:27][C@H:25]([NH:24][C:21]([C:18]1[CH:17]=[N:16][C:15]([O:14][CH2:13][C:12]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)=[N:9][O:10][CH:11]=2)=[CH:20][N:19]=1)=[O:23])[CH3:26]

Participants

3

Reactant 2

HCID 80307L-AlaninolHCID 684440725-[3-(4-Chloro-phenyl)-isoxazol-4-ylmethoxy]-pyrazine-2-carboxylic acid

Product 1

HCID 469379045-[3-(4-Chloro-phenyl)-isoxazol-4-ylmethoxy]-pyrazine-2-carboxylic acid ((R)-2-hydroxy-1-methyl-ethyl)-amideYield 47%

Procedure

As described for example 17b, 5-[3-(4-chloro-phenyl)-isoxazol-4-ylmethoxy]-pyrazine-2-carboxylic acid (80 mg, 0.24 mmol) was converted, using L-alaninol instead of D-alaninol, to the title compound (44 mg, 47%) which was obtained as a white solid. MS: m/e=389.0 [M+H]+.

Sources & evidence

ORD record
ord-074228ab254447d6a2b1a0901648fc1f
Source dataset
uspto-grants-2011_03
Patent number
US07902201B2

Reaction notes

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