Sodium Hydroxide → HCID 178507261, compound

Participants

Reaction Steps

17.33 g of stannous chloride was added to a hydrated ethanol (120 ml of ethanol+1.2 ml of water) suspension containing 6.08 g of N-benzyloxycarbonyl-trans-4-[(6-nitro-1-indolinyl)carbonyl]cyclohexylamine (the compound obtained in the same manner as in Reference Example 13-1 before deprotection), and the mixture was refluxed under argon atmosphere for 4.5 hours. An aqueous 10% sodium hydroxide solution was added to the reaction mixture to adjust pH of the mixture to pH 9 to 10, the mixture was diluted with 300 ml of chloroform and dried over anhydrous magnesium sulfate, and then, the insolubles were removed by filtration. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (solvent: chloroform-ethyl acetate (2:1)) to obtain 4.72 g of N-benzyloxycarbonyl-trans-4-[(6-amino-1-indolinyl)carbonyl]cyclohexylamine. (2) 0.12 ml of pyridine and 0.104 ml of acetic anhydride were added to 10 ml of a methylene chloride solution containing 396 mg of the compound obtained in the above (1), and the mixture was stirred for 5 hours. 5% hydrochloric acid was added to the reaction mixture and the mixture was extracted with chloroform. The extracted layer was successively washed with water and an aqueous saturated sodium bicarbonate solution and dried over anhydrous sodium sulfate, and then, the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (solvent: chloroform-ethyl acetate (1:1)).

Provenance & Evidence