Hydrochloric Acid → (2S)-1-(1,2-Dioxo-3,3-dimethylpentyl)azetidine-2-carboxylic acid

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Reaktionsgleichung

C[O:2][C:3]([C@@H:5]1[CH2:8][CH2:7][N:6]1[C:9](=[O:17])[C:10](=[O:16])[C:11]([CH3:15])([CH3:14])[CH2:12][CH3:13])=[O:4].CCOCC.[Li+].[OH-].Cl>O.CO>[O:17]=[C:9]([N:6]1[CH2:7][CH2:8][C@H:5]1[C:3]([OH:4])=[O:2])[C:10](=[O:16])[C:11]([CH3:14])([CH3:15])[CH2:12][CH3:13]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a solution of (2S)-Methyl-1-(1,2-dioxo-3,3-dimethylpentyl)-azetidine-2-carboxylate from Reference Example 3 (0.64 g, 2.65 mmol) in a 1:1 mixture of ether:methanol (20.0 mL) was added LiOH in water (4.9 mL, 1N solution) at about 0° C. The mixture was stirred at about 0° C. for about 30 minutes and then at about room temperature overnight. The pH was adjusted to about pH 1 by adding 1N HCl, then the mixture was diluted with water and extracted with dichloromethane. The organic layers were washed with brine and dried over sodium sulfate and then concentrated to give 0.40 g (67% yield) of the product as a yellow semisolid. 1H NMR (DMSO) δ 0.77-0.83 (m, 3H); 1.20-1.29 (series of s, 6H); 1.49-2.84 (series of m, 4H); 4.02-4.43 (series of m, 2H); 5.01-5.31 (series of dd, 1H); 6.10-6.80 (br, 1H).

Aufarbeitung

customat about room temperature
customovernight
extractionextracted with dichloromethane
washThe organic layers were washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-72421745bf2e45eb972db3ffbc71cdf1
Quelldatensatz: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06544976B1

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