Benzyl 6-aminoamido-n-hexanoylcarbolinecarboxylate, its preparation, activity and application
A technology of benzyl carboxylate and amino, applied in organic chemistry, drug combination, antineoplastic drugs, etc.
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Embodiment 1
[0016] Example 1 Preparation of (3S)-2,3,4,9-tetrahydro-β-carboline-3-carboxylic acid benzyl ester (1)
[0017] Slowly add 1.5mL concentrated H to 300mL water under ice bath 2 SO 4 , Stir for 3min. Then 5.00 g (15.1 mmol) L-tryptophan benzyl ester hydrochloride and 6 mL formaldehyde solution (40%) were added. After stirring at room temperature for 72 hours, TLC showed that L-tryptophan benzyl ester hydrochloride disappeared. The pH of the reaction solution was adjusted to 7 with concentrated ammonia water in an ice bath and filtered. The filter cake was dissolved with 100 mL of ethyl acetate, and the resulting solution was washed with a saturated aqueous sodium chloride solution (40 mL×3), and then dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane: methanol = 90:1) to obtain 1.9 g (41%) of the target compound as a yellow oily solid. ESI-MS(m...
Embodiment 2
[0018] Example 2 Preparation of 6-tert-butoxycarbonylaminocaproic acid (2)
[0019] 5.00 g (38.2 mmol) of 6-aminocaproic acid (EACA) was suspended in 50 mL of distilled water. The obtained suspension was added with 10 mL of sodium hydroxide aqueous solution (2M) under ice bath and stirred until dissolved. Add 9.2g (42.2mmol) (Boc) to the resulting solution 2 A solution of O and 20 mL of dioxane was adjusted to pH 9 with aqueous sodium hydroxide (2M) and stirred for 30 min. Remove the ice bath, stir at room temperature until TLC shows the disappearance of 6-aminocaproic acid. Saturated KHSO for reaction solution under ice bath 4 The pH of the aqueous solution was adjusted to 7, and the dioxane was removed by concentration under reduced pressure. Saturated KHSO for reaction solution under ice bath 4 The pH of the aqueous solution was adjusted to 2, and it was extracted with ethyl acetate (50 mL×3). The ethyl acetate layer was washed with saturated NaCl aqueous solution (40 mL×3)...
Embodiment 3
[0020] Example 3 Preparation of (3S)-N-(6-Boc-amino-n-hexanoyl)-2,3,4,9-tetrahydro-β-carboline-3-carboxylic acid benzyl ester (3)
[0021] Dissolve 4.15g (18mmol) Boc-6-aminocaproic acid with 80mL of anhydrous tetrahydrofuran, add 2.46g (18.2mmol) N-hydroxybenzotriazole (HOBt) and 4.04g (19.6mmol) N, N-Dicyclohexylcarbodiimide (DCC), stirring for 60 minutes. Afterwards, a solution of 5.06 g (16.5 mmol) of (3S)-2,3,4,9-tetrahydro-β-carboline-3-carboxylic acid benzyl ester and 80 mL of anhydrous tetrahydrofuran was added to the obtained reaction solution. The reaction mixture was adjusted to pH 9 with N-methylmorpholine (NMM) in an ice bath, and stirred at room temperature for 24 hours. TLC showed that (3S)-2,3,4,9-tetrahydro-β-carboline-3-carboxylic acid benzyl ester disappeared. The reaction solution was filtered, the filtrate was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate. Saturated NaHCO 3 Wash with aqueous solution (40mL×3), wash wit...
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