Lithium Hydroxide → 1-[(cis)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]-1H-imidazole-4-carboxylic acid

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Reaction Steps

A mixture of ethyl 1-[(cis)1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]-1H-imidazole-4-carboxylate (for a preparation see Intermediate 82) (1.8 g, 4.2 mmol), methanol (15 mL), and lithium hydroxide (1M in water, 15 mL) was stirred at room temperature for 6 h then most of the methanol was removed in vacuo. The residue was diluted with water (15 mL) and acidified with glacial acetic acid. The resulting aqueous phase was extracted with AcOEt (3×30 mL). The combined organic phases were washed with brine, dried over MgSO4 and concentrated in vacuo to give 1-[(cis)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]-1H-imidazole-4-carboxylic acid (1.1 g, 2.75 mmol, 65%) as a colourless solid.

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