Rosuvastatin calcium intermediate and method for preparing rosuvastatin calcium intermediate and rosuvastatin calcium
A technology for rosuvastatin and its intermediates, which is applied in the field of organic drug synthesis, can solve the problems of high preparation price, high production cost, and technical difficulty, and achieve the effects of high optical purity, quality improvement, and cost reduction
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Embodiment 1
[0033] Example 1: Preparation of 3-hydroxy-5-oxo-hexanoic acid tert-butyl ester
[0034] Add 72g of tert-butyl 3-oxopropionate, 6.1g of tetrahydropyridine, and 300ml of acetone into a 500ml reaction bottle, stir and react at 25-30°C for 2-3 hours, until the raw materials basically disappear as detected by TLC, and desolvate under reduced pressure within 45°C To dryness, 97.7g of compound B was obtained, the purity of which was detected by GC was 91.1%, and the yield was 89.3%.
[0035] The product is yellow liquid. 1HNMR(400MHz, CDCl3)δ4.47–4.35(m,1H),3.48(s,1H),2.65(dd,J=8.3,6.2Hz,2H),2.42(d,J=6.4Hz,2H), 2.19(s,3H),1.44(d,J=5.2Hz,9H).
Embodiment 2
[0036] Example 2: Preparation of 3-hydroxy-5-oxo-hexanoic acid methyl ester
[0037] Add 68g of methyl 3-oxopropionate, 6.1g of tetrahydropyridine, and 300ml of acetone into a 500ml reaction bottle, stir and react at 25-30°C for 2-3 hours, until the raw materials basically disappear as detected by TLC, and precipitate under reduced pressure within 45°C to After drying, 95.7g of compound B' was obtained, the purity of which was detected by GC was 91.5%, and the yield was 89.6%.
Embodiment 3
[0038] Example 3: 6-trans-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)-5-pyrimidine]vinyl-3- Preparation of tert-butyl hydroxy 5-oxopentanoate
[0039] Add 97.7g of compound B and 156.2g of compound C, 580ml of ethanol, 50ml of 5% liquid caustic soda solution into a 1000ml reaction bottle, heat to 25-30°C, stir and react for 3-4 hours, use TLC to detect that the reaction is basically complete, add dilute hydrochloric acid Adjust the pH to neutral, desolvate under reduced pressure to semi-dry within 55°C, add 500ml of ethyl acetate to dissolve, then wash twice with 150ml of water, and desolventize to dryness to obtain 190g of compound D. The purity of HPLC is 93.5%, and the yield is 74.8%. .
[0040] Wherein the NMR data of compound D are:
[0041] 1HNMR (400MHz, CDCl3) δ7.67(m,2H),7.08(m,2H),6.25-6.29(m,1H),5.48-5.54(m,1H),4.47–4.35(m,2H),3.56 (s,3H),3.50(s,3H),δ3.48(s,1H),3.35-3.42(m,1H),2.65(dd,J=8.3,6.2Hz,2H),2.42(d,J =6.4Hz, 2H), 1.44(d, J=5.2Hz, ...
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