Ethanol → ethyl 2-[(2-{(4S)-4-[(1E,3R)-3-hydroxy-4,4-dimethyl-1-octenyl]-2-oxo-1,3-oxazolidin-3-yl}ethyl)thio]-1,3-thiazole-4-carboxylate

Reaktionsgleichung

[CH2:1]([C:5]1([CH:9]([OH:30])/[CH:10]=[CH:11]/[C@H:12]2[C@H:16](C)[O:15][C:14](=[O:18])[N:13]2[CH2:19][CH2:20][S:21][C:22]2[S:23][CH:24]=[C:25]([C:27]([OH:29])=[O:28])[N:26]=2)CC[CH2:6]1)[CH2:2][CH2:3][CH3:4].[C:31]([O-])(=O)[CH3:32].[Na+].[CH2:36](O)C>>[OH:30][C@@H:9]([C:5]([CH3:6])([CH3:36])[CH2:1][CH2:2][CH2:3][CH3:4])/[CH:10]=[CH:11]/[C@H:12]1[CH2:16][O:15][C:14](=[O:18])[N:13]1[CH2:19][CH2:20][S:21][C:22]1[S:23][CH:24]=[C:25]([C:27]([O:29][CH2:31][CH3:32])=[O:28])[N:26]=1

Komponenten

Edukt 3

HCID 702Ethanol

HCID 517045Sodium Acetate

HCID 668574432-[(2-{(4S,5S)-4-[(1E)-3-(1-butylcyclobutyl)-3-hydroxy-1-propenyl]-5-methyl-2-oxo-1,3-oxazolidin-3-yl}ethyl)sulfanyl]-1,3-thiazole-4-carboxylic acid

Produkt 1

HCID 66857441ethyl 2-[(2-{(4S)-4-[(1E,3R)-3-hydroxy-4,4-dimethyl-1-octenyl]-2-oxo-1,3-oxazolidin-3-yl}ethyl)thio]-1,3-thiazole-4-carboxylate

Versuchsvorschrift

To a solution of ethyl ester of the compound 34-4 (175 mg) in ethanol (3 mL) was added p-toluenesulfonylhydrazide (6 g) and the solution was dissolved at 90° C. Sodium acetate (4.5 g) was added thereto and the solution was stirred for 10 Hours. After standing to cool to room temperature, the reaction solution was concentrated. Ethyl acetate and water was added thereto and the solution was extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, an aqueous saturated sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate and concentrated. The obtained residue was purified by column chromatography on silica gel (Fuji-silysia, FL60D, 60 mL, n-hexane:ethyl acetate=9:11). The title compound having the following physical data was obtained by the same procedure by the same procedure as the reaction of example 8 using the obtained residue instead of the compound 7.