Levovitamin c-2-oxoacetyl-pakpak, its synthesis, activity and application
A technology of C-2-, oxyacetyl, which is applied in L-dimensional C-2-oxyacetyl-PAKPAK, can solve the problems of untreated ischemic stroke, unable to antagonize rat aortic strip relaxation, and unsatisfactory
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Embodiment 1
[0025] Embodiment 1 prepares levovitamin C-2-ethyl oxyacetate (1)
[0026]To a solution of 1.14g (28mmol) NaH (60%) and 10mL of anhydrous dimethylformamide (DMF) at 0°C, add 5.00g (28mmol) of levovitamin C in batches, bubbles appear, wait until there are no bubbles Finally, 5.42 g (28 mmol) of ethyl bromoacetate was added dropwise, and the reaction was stirred for 12 hours, and TLC showed that the reaction was complete. The solvent was removed from the reaction mixture under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain 3.49 g (49%) of the title compound as a colorless syrup. ESI-MS(m / e):261[M-H] - ;Mp:177-179℃;[α] D 25 =-12.1 (c=0.1, MeOH), IR (KBr, cm -1 ):3333,1761,1676,1269,1247; 1 HNMR (300MHz, DMSO-d6): δ / ppm=4.94(m, 2H), 4.85(s, 1H), 4.15(q, J=0.6Hz, 2H), 3.83(m, 1H), 3.48(m, 2H), 1.20 (t, J=0.6Hz, 3H).
Embodiment 2
[0027] Embodiment 2 prepares L-vitamin C-2-oxoacetic acid (2)
[0028] Dissolve 3.49 g (13.3 mmol) of ethyl levovitamin-2-oxyacetate (1) in 10 mL of methanol, add 1 mL of water with stirring in an ice bath, and adjust the pH value to 12 with 2M NaOH aqueous solution. Stir in an ice bath for 12 h, and monitor the completion of the reaction by TLC. The reaction mixture was washed with 5% KHSO 4 The aqueous solution was adjusted to pH 7, and concentrated under reduced pressure to remove the solvent to obtain 2.52 g (89%) of the title compound as a colorless powder. ESI-MS(m / e):233[M-H] - .
Embodiment 3
[0029] Embodiment 3 prepares Boc-Pro-OSu
[0030] Dissolve 5.50g (25.6mmol) Boc-Pro in 30mL of anhydrous tetrahydrofuran (THF), add 6.32g (30.6mmol) dicyclohexylcarbodiimide (DCC) under ice-cooling, stir for 30min, add 3.24g (28.1 mmol) N-hydroxysuccinimide (HOSu), stirred for 12 h, and the reaction was monitored by TLC to complete. Dicyclohexylurea (DCU) was removed by filtration under reduced pressure, the filtrate was concentrated to dryness under reduced pressure, and the obtained residue was dissolved in ethyl acetate, and then washed with saturated NaHCO 3 The aqueous solution was washed three times, and the saturated NaCl aqueous solution was washed three times, and the organic phase was washed with anhydrous NaCl 2 SO 4 It was dried for 8 h, filtered under reduced pressure, and the filtrate was concentrated under reduced pressure to remove the solvent to obtain 6.64 g (83.2%) of the title compound as a colorless powder. ESI-MS(m / e):313[M+H] + .
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