DELAPRIL
DELAPRIL
CAS: 83435-66-9
Molecular Formula: C26H32N2O5
DELAPRIL - Names and Identifiers
DELAPRIL - Physico-chemical Properties
| Molecular Formula | C26H32N2O5 |
| Molar Mass | 452.54 |
| Storage Condition | Sealed in dry,2-8°C |
| Physical and Chemical Properties | Chemical Properties Dilapril Hydrochloride (Delapril Hydrochloride):C26H32N2O5?HCl. [83435-67-0]. Colorless flake crystals obtained from acetone-hydrochloric acid, melting point 166-170 ℃ (decomposition). [α]D22 18.5(C = 1, methanol). |
| Use | Use of angiotensin converting enzyme inhibitor, the ACE blocking activity is 10 times that of captopril, has a good blocking effect on ACE in plasma, and has a long duration. For primary hypertension, renal hypertension, renal vascular hypertension. |
DELAPRIL - Upstream Downstream Industry
| Raw Materials | Magnesium sulfate Ethyl chloroformate BROMOCHLORODIFLUOROMETHANE 2-Indanone N-Carbobenzyloxy-L-alanine tert-Butyl glycinate |
DELAPRIL - Production method
Using 2-indanone as raw material, it is obtained through a 5-step reaction.
2-indanone (40g), 78g of tert-butyl glycine? H3P03 complex (for preparation, see Anderson G W,et a1.JACS,1960,82:3359), 150ml of water and 300ml of methanol were mixed, and 23g of NaBH3CN were added in batches within 15min under water bath and stirring. Add and stir for 4 hours. After adding 400ml of 20% phosphoric acid and 200ml of water to dilute, extract with 500ml chloroform. The extract is dried with anhydrous sodium sulfate and concentrated under reduced pressure. The remaining oil was crystallized with ethanol-water to obtain 47% colorless prismatic crystal compound (I) with 63% yield and melting point of 54-55 ℃.
21.8g N-benzyloxycarbonyl-L-alanine and 12.8ml triethylamine were dissolved in 200ml tetrahydrofuran, and 8.5g ethyl chloroformate was dropped at -15 ℃ and stirred. After adding, stir for 15min. Then drop 22g of compound (I) at 100ml chloroform below -10 ℃. After adding, continue stirring at room temperature for 1h. The reaction liquid was poured into 500rnl of water. The separated organic layer is concentrated under reduced pressure, the remaining liquid is dissolved in 300ml of ethyl acetate, washed with lmol/L sodium hydroxide (2 × 50 m1), 50ml of water, 20% phosphoric acid (2 × 50 m1) and 50ml of water in turn, and dried with anhydrous magnesium sulfate. 35g of colorless oily compound (II) was concentrated under reduced pressure with 87% yield.
35g of compound (II) and 7g of oxalic acid are dissolved in 300ml of methanol and reduced at atmospheric pressure under the catalysis of 10% palladium-carbon (50% wet volume, 8.5g). Filter off the catalyst, add 500ml ether after the filtrate is concentrated under reduced pressure. The colorless crystals precipitated were filtered and collected to obtain 21.8g compound (Ⅲ) with 68% yield, melting point 138~141 ℃, [α]D22 +20.4 (C = 1, methanol).
21g of compound (Ⅲ), 4.1g of sodium acetate, 10ml of acetic acid, 25g of ethyl 2-oxo-4-phenylbutyrate, 25g3A molecular sieve and 200ml of ethanol were mixed and hydrogenated at atmospheric pressure under the catalysis of 30g Raney Ni. When hydrogen absorption stops. The upper layer solution is separated, and the catalyst is washed with ethanol. The lotion and the upper layer solution are combined and concentrated under reduced pressure. The remainder is dissolved in 500ml of ethyl acetate, washed with sodium bicarbonate solution and water, and dried with anhydrous magnesium sulfate. Concentrated under reduced pressure to obtain a light yellow liquid, chromatography with silica gel, acetone-benzene (1:9) elution. The eluted second component was collected to obtain 16.5g compound (Ⅳ) with a yield of 61%,[α]D22-12.6 (C = 1, methanol).
Dissolve 5g of compound (IV) in 5ml of acetic acid, add 20ml of 25% hydrogen bromide-acetic acid solution, stir for 10min, add 300ml of ether to dilute. The colorless crystals precipitated by filtration were collected to obtain 5g of diapril hydrobromide with 95% yield, melting point 180-183 ℃,[α]D22 +15.6 (C = 1.4, methanol).
Under stirring, 16.2g of diapril hydrobromide was added to a solution of 500ml of ethyl acetate, 33g of sodium bicarbonate and 500ml of water. After acidification with 1mol/L hydrochloric acid to Ph = 4, the ethyl acetate layer is separated, washed with water, and dried with anhydrous magnesium sulfate. Then 20ml of 7mol/L hydrogen chloride-ethyl acetate solution was added, and the solution was concentrated under reduced pressure. The remainder is added with 250ml of ether and 250ml of petroleum ether to precipitate deazapril hydrochloride (11g, yield 74%), and recrystallized with acetone-lmol/L hydrochloric acid to obtain colorless flake crystalline deazapril hydrochloride, melting point 166-170 ℃ (decomposition),[α]D22 +18.5 (C = 1, methanol).
The compound (I) obtained above can also be directly condensed with the compound (V) to obtain the compound (IV), and then hydrolyzed to form a salt to obtain diazopril hydrochloride. The preparation of compound (V) can refer to the preparation method of other angiotensin converting enzyme inhibitors. The condensation of compound (I) and compound (V) is carried out as follows.
0.2g compound (V) and 0.22g compound (I) are soluble. 10ml dimethylformamide, add a solution of 0.2gDEPC in 5ml dimethylformamide dropwise under stirring. After adding, add 0.15g of triethylamine in 1ml of dimethylformamide solution and stir for 1h. After dilution with 100ml of water, extract with 300ml of ethyl acetate. The extract was washed with 10% phosphoric acid (2 × 50 m1), 20ml of 1mol/L sodium hydroxide and water, and dried with anhydrous magnesium sulfate. The oily residue after decompression concentration was eluted with silica gel chromatography and hexane-ethyl acetate (2:1~1:1). 0.22g of colorless oily compound (Ⅳ) was obtained with a yield of 68%,[α]D22-12.5 (c = 0.9, methanol).
Last Update：2024-04-09 01:59:49
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CAS: 83435-66-9
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CAS: 83435-66-9
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View History
Raw Materials for DELAPRIL
Magnesium sulfate
Ethyl chloroformate
BROMOCHLORODIFLUOROMETHANE
2-Indanone
N-Carbobenzyloxy-L-alanine
tert-Butyl glycinate
Ethyl chloroformate
BROMOCHLORODIFLUOROMETHANE
2-Indanone
N-Carbobenzyloxy-L-alanine
tert-Butyl glycinate