3-[1-(3,5-dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid (3aR, 5aS, 8aS, 8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethyl ester → 3-[1-(3,5-Dimethyl-1h-pyrrol-2-yl)-meth-(z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid (3r, 4s, 5r)-3,4,5,6-tetrahydroxy-tetrahydro-pyran-2-ylmethyl ester

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Reaction Steps

3-[1-(3,5-Dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid (3aR,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4′,5′-d]pyran-5-ylmethyl ester was dissolved in the mixture of 5.0 mL of 6 N HCl aq. and 20 mL of THF. The resultant mixture was stirred at room temperature for 3 h and 40 C for 1 h and concentrated. The residue was washed with ethyl acetate and THF and dried to give 133 mg (60%) of 3-[1-(3,5-dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid (3R,4S,5R)-3,4,5,6-tetrahydroxy-tetrahydro-pyran-2-ylmethyl ester as a yellow solid.

Provenance & Evidence