Preparation method of chiral warfarin and chiral warfarin derivatives
A derivative and chiral technology, which is applied in the field of preparation of coumarin anticoagulants—chiral warfarin and its derivatives, can solve the problem of weakening effect, increasing coagulation effect, failing to obtain good experimental results, etc. problem, to achieve the effect of low cost and easy operation
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Embodiment 1
[0043] 1) Preparation of intermediate product substituted benzylidene acetone. Reaction formula:
[0044]
[0045] Steps:
[0046] A 50ml single neck round bottom flask was charged with benzaldehyde (0.02mol) and acetone (0.56mmol). Then add 0.5ml of 10% NaOH aqueous solution, then add 2ml of H 2 O. Stir at room temperature for 3h. After the reaction, the pH was adjusted with dilute HCl to make the solution neutral. Separation and purification (vacuum distillation) to obtain a viscous oily liquid, after cooling to obtain a pale yellow solid-benzylidene acetone (150 ~ 160 ℃ / 3333Pa (7mmHg)).
[0047] 2) Preparation of chiral warfarin. Reaction formula:
[0048]
[0049] Steps:
[0050] 10ml reaction test tube, add 4-hydroxycoumarin (0.1m mol), benzylidene acetone (0.12m mol), chiral primary amine catalyst (5m mol%), lithium perchlorate (5mmol%), Acetic acid (1mmol, 10eq), and finally add 2ml of 1,4-dioxane. Stir at room temperature for 24 hours, and quench by adding water after th...
Embodiment 2
[0061] 1) Preparation of intermediate product 4-methylbenzylideneacetone, reaction formula:
[0062]
[0063] Steps:
[0064] A 50ml single neck round bottom flask was charged with 4-methylbenzaldehyde (0.02mol) and acetone (0.56mmol). Then add 0.5ml of 10% NaOH aqueous solution, then add 2ml of H 2 O. Stir at room temperature for 3h. After the reaction, the pH was adjusted with dilute HCl to make the solution neutral. Separation and purification (vacuum distillation) to obtain a viscous oily liquid, after cooling to obtain a pale yellow solid-benzylidene acetone (150-160°C / 3333Pa(7mmHg)).
[0065] 2) Preparation of chiral warfarin derivatives, reaction formula:
[0066]
[0067] Steps:
[0068] 10ml reaction test tube, add 4-hydroxycoumarin (0.1621g, 0.1mmol, 1eq), intermediate product 4-methylbenzylideneacetone (0.220g, 0.12mmol, 1.2eq), chiral primary amine catalyst in one go (5mmol%), lithium perchlorate (5mmol%), acetic acid (1mmol, 10eq), and finally add 2ml of 1,4-dioxane. ...
Embodiment 3
[0070] 1) Preparation of the intermediate product 2-methoxybenzylideneacetone. Reaction formula:
[0071]
[0072] Steps:
[0073] A 50ml single neck round bottom flask was charged with 2-methoxybenzaldehyde (0.02mol) and acetone (0.56mmol). Then add 0.5ml of 10% NaOH aqueous solution, then add 2ml of H 2 O. Stir at room temperature for 3h. After the reaction, the pH was adjusted with dilute HCl to make the solution neutral. Separate and purify the fractions (distilled under reduced pressure) to obtain a viscous oily liquid. After cooling, obtain a light yellow solid-benzylidene acetone (150-160℃ / 3333Pa(7mmHg))
[0074] 2) Preparation of chiral warfarin derivatives, reaction formula:
[0075]
[0076] (3);
[0077] Steps:
[0078] 10ml reaction test tube, add 4-hydroxycoumarin (0.1mmol), intermediate product 2-methoxybenzylideneacetone (0.12mmol), chiral primary amine catalyst (5mmol%), lithium perchlorate ( 5mmol%), acetic acid (1mmol, 10eq), and finally add 2ml of 1,4-dioxane. S...
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