tert-Butyl acetate → (RS)-3-hydroxy-3-(6-methoxy-[1,5]naphthyridin-4-yl)-propionic acid tert-butyl ester

HRID 1640509Notes

Reaction equation

HRID 1640509 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[CH:13]=[O:14].[C:15]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])(=[O:17])[CH3:16]>CC(=O)OCC>[C:19]([O:18][C:15](=[O:17])[CH2:16][CH:13]([OH:14])[C:6]1[C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[N:4]=2)[N:9]=[CH:8][CH:7]=1)([CH3:22])([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 10908tert-Butyl acetateHCID 665231381,5-Naphthyridine-4-carboxaldehyde, 6-methoxy-

Product 1

HCID 66737830(RS)-3-hydroxy-3-(6-methoxy-[1,5]naphthyridin-4-yl)-propionic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The aldol reaction between 6-methoxy-[1,5]naphthyridine-4-carbaldehyde (1.9 g, 10 mmol, WO 2006/032466) and tert-butyl acetate (1.2 g, 10.5 mmol) was carried out as described in the literature (J. Org. Chem. (1990), 55, 4744-4750). The title compound was isolated after chromatography on SiO2 (Hex/EA 1:1) as a beige solid (2.33 g, 77% yield).

Sources & evidence

ORD record
ord-da09ce391ee3424ea0b16f1e2f68c2c1
Source dataset
uspto-grants-2012_02
Patent number
US08114867B2

Reaction notes

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