N-Benzenesulfonyl-(L)-prolyl-2-amino-2-norbornanecarboxylic acid, methyl ester → N-Benzenesulfonyl-(L)-prolyl-2-amino-2-norbornanecarboxylic acid
Reaktionsgleichung
[C:1]1([S:7]([N:10]2[CH2:28][CH2:27][CH2:26][C@H:11]2[C:12]([C:14]23[CH2:20][CH:17]([CH2:18][CH2:19]2)[CH2:16][C:15]3([NH2:25])[C:21]([O:23]C)=[O:22])=[O:13])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[OH-].[Na+].CO>[C:1]1([S:7]([N:10]2[CH2:28][CH2:27][CH2:26][C@H:11]2[C:12]([C:14]23[CH2:20][CH:17]([CH2:18][CH2:19]2)[CH2:16][C:15]3([NH2:25])[C:21]([OH:23])=[O:22])=[O:13])(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Komponenten
4
Versuchsvorschrift
A solution of N-phenylsulfonyl-(L)-prolyl-2-amino-2-norbornanecarboxylic acid, methyl ester (210 mg, 0.2 mmol) in 3 mL of 1:1 aqueous sodium hydroxide (1 M) and methanol was stirred at room temperature for 2 weeks. The reaction was quenched with concentrated hydrochloric acid (0.2 mL), and the resulting mixture was partitioned between saturated salt solution and ethyl acetate. The product was extracted with ethyl acetate and was purified by flash chromatography on silica gel eluted with 100:5:1 methylene chloride/methanol/acetic acid to give the product as a mixture of diastereomers.