ChemicalBook CAS DataBase List 2H-Isoindole-2-butanoic acid, γ-(aminocarbonyl)-1,3-dihydro-4-hydroxy-1-oxo-, 1,1-dimethylethyl ester, (γS)-

2H-Isoindole-2-butanoic acid, γ-(aminocarbonyl)-1,3-dihydro-4-hydroxy-1-oxo-, 1,1-dimethylethyl ester, (γS)- synthesis

11synthesis methods

Product Name:2H-Isoindole-2-butanoic acid, γ-(aminocarbonyl)-1,3-dihydro-4-hydroxy-1-oxo-, 1,1-dimethylethyl ester, (γS)-
CAS Number:1560678-51-4
Molecular formula:C17H22N2O5
Molecular Weight:334.37

2H-Isoindole-2-butanoic acid, γ-(aminocarbonyl)-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1,3-dihydro-1-oxo-, 1,1-dimethylethyl ester, (γS)-

1560678-56-9
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2H-Isoindole-2-butanoic acid, γ-(aminocarbonyl)-1,3-dihydro-4-hydroxy-1-oxo-, 1,1-dimethylethyl ester, (γS)-

1560678-51-4
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Yield:1560678-51-4 67%

Reaction Conditions:

with tetrabutyl ammonium fluoride in tetrahydrofuran; for 0.5 h;

Steps:

5.5 (S)-tert-Butyl 5-amino-4-(4-hydroxy-1-oxoisoindolin-2-yl)-5-oxopentanoate (5f)

5e (545 mg, 1.21 mmol) was dissolved in THF (3 mL) at room temperature, tetrabutylammonium fluoride in THF (1 M, 1.5 mL, 1.5 mmol) was added and stirred for 30 min. The mixture was diluted with water (20 mL), then extracted with ethyl acetate (3 x 20 mL). The combined organic phases were dried over anhydrous sodium sulfate, and after filtration, the filtrate was concentrated to dryness under reduced pressure, and the residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=1/1 to 0/100) to obtain The desired product 5f (270 mg, 67%).

References:

CN113896711,2022,A Location in patent:Paragraph 0182-0184; 0204-0207