Sulfuryl chloride → Quinaldic Acid

Reaktionsgleichung

C(OC(=O)N[C@H:8]([C:13](=O)[NH:14][CH:15]1[CH2:21][CH2:20][CH2:19]NC[CH:16]1[OH:22])[CH2:9][CH:10]([CH3:12])C)(C)(C)C.S(Cl)(Cl)(=O)=[O:26]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[N:14]1[C:13]2[C:19](=[CH:12][CH:10]=[CH:9][CH:8]=2)[CH:20]=[CH:21][C:15]=1[C:16]([OH:22])=[O:26]

Komponenten

Versuchsvorschrift

To a solution of [(S)-1-(3-hydroxy-azepan-4-ylcarbamoyl)-3-methyl-butyl]-carbamic acid tert butyl ester of Example 1g (2.5 g, 7.28 mmol) in CH2Cl2 (100 mL) and sat. NaHCO3 (400 mL) was added the solution of 2-pyridinesulfonyl chloride-N-oxide (27 mL, 102 mg/mL) dropwise in portions. As the addition proceeds additional sat. NaHCO3 is added in order to maintain the pH at approximately 8-9. Upon complete addition of the sulfonylchloride the reaction is stirred for an additional hour whereupon the organic layer was removed and washed with brine. The organic layer was evaporated and the residue chromatographed (5% methanol:dichloromethane) to provide 2.5 g of the title compound: MS (El) 500 (M+H+).