4-Formylbenzoic acid → rac-N-(3-{4-[5-(4-formyl-phenyl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide

HRID 1958821Notes

Reaction equation

HRID 1958821 reaction equation
[OH:1][CH2:2][C:3]([NH:5][CH2:6][CH:7]([OH:22])[CH2:8][O:9][C:10]1[C:15]([CH3:16])=[CH:14][C:13]([C:17](=[NH:20])[NH:18][OH:19])=[CH:12][C:11]=1[CH3:21])=[O:4].[CH:23]([C:25]1[CH:33]=[CH:32][C:28]([C:29](O)=O)=[CH:27][CH:26]=1)=[O:24].C(C1C=C(C2ON=C(C3C=C(C)C(OCC(O)CNC(=O)CO)=C(C)C=3)N=2)C=CC=1)=O>>[CH:23]([C:25]1[CH:33]=[CH:32][C:28]([C:29]2[O:19][N:18]=[C:17]([C:13]3[CH:14]=[C:15]([CH3:16])[C:10]([O:9][CH2:8][CH:7]([OH:22])[CH2:6][NH:5][C:3](=[O:4])[CH2:2][OH:1])=[C:11]([CH3:21])[CH:12]=3)[N:20]=2)=[CH:27][CH:26]=1)=[O:24]

Participants

4

Reactant 3

HCID 120884-Formylbenzoic acidHCID 87208794HCID 87208794, compoundHCID 178426660HCID 178426660, compound

Product 1

HCID 87208910rac-N-(3-{4-[5-(4-formyl-phenyl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide

Procedure

The title compound was prepared from rac-2-hydroxy-N-{2-hydroxy-3-[4-(N-hydroxycarbamimidoyl)-2,6-dimethyl-phenoxy]-propyl}-acetamide and 4-formyl-benzoic acid in analogy to (rac)-N-(3-{4-[5-(3-formyl-phenyl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide. LC-MS: tR=0.88 min; [M+1]+=426.36.

Sources & evidence

ORD record
ord-284709f051d04eff8cb859eb38ba4dd2
Source dataset
uspto-grants-2013_04
Patent number
US08410151B2

Reaction notes

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