Beta-Alanine → 6-[3-(Benzyloxy)-2-methyl-4-oxopyridin-1(4H)-yl]hexanoic acid

HRID 1165907Notes

Reaction equation

HRID 1165907 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].[CH2:10]([O:17][C:18]1[C:23](=[O:24])[CH:22]=[CH:21]O[C:19]=1[CH3:25])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.NCCC(O)=O>>[CH2:10]([O:17][C:18]1[C:23](=[O:24])[CH:22]=[CH:21][N:1]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8])[C:19]=1[CH3:25])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 239Beta-AlanineHCID 5646-Aminohexanoic AcidHCID 14901193-Benzyloxy-2-methyl-4-pyrone

Product 1

HCID 134232836-[3-(Benzyloxy)-2-methyl-4-oxopyridin-1(4H)-yl]hexanoic acidYield 70%

Procedure

6-Aminocaproic acid is reacted with 3-benzyloxy-2-methyl-4-pyrone in an exactly analogous procedure to that described in Example 2 for the reaction of the latter compound with β-alanine to give 3-benzyloxy-1-(5'-carboxypentyl)-2-methylpyrid-4-one in 70% yield, this compound being obtained after recrystallisation from ethanol/acetone (1:1 v/v) as white crystals, m.p. 145°-147° C.

Sources & evidence

ORD record
ord-969718ee2fa748e3994b779081edeea5
Source dataset
uspto-grants-1990_03
Patent number
US04912118

Reaction notes

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