Water → Rosuvastatin

HRID 578739

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HRID 578739 반응식
[CH3:1][CH:2]([C:4]1[N:9]=[C:8]([N:10]([S:12]([CH3:15])(=[O:14])=[O:13])[CH3:11])[N:7]=[C:6]([C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)[C:5]=1/[CH:23]=[CH:24]/[C@@H:25]([OH:33])[CH2:26][C@@H:27]([OH:32])[CH2:28][C:29]([OH:31])=[O:30])[CH3:3].C([NH-])CCC.O.C(N)(C)(C)C>CC(O)C>[CH3:3][CH:2]([C:4]1[N:9]=[C:8]([N:10]([S:12]([CH3:15])(=[O:13])=[O:14])[CH3:11])[N:7]=[C:6]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[C:5]=1/[CH:23]=[CH:24]/[C@@H:25]([OH:33])[CH2:26][C@@H:27]([OH:32])[CH2:28][C:29]([OH:31])=[O:30])[CH3:1]

참가 물질

5

반응물 3

HCID 962WaterHCID 6385Tert-ButylamineHCID 86699893Rosuvastatin n-butylamide

생성물 1

HCID 446157Rosuvastatin수율 112.1%

시약·촉매·용매 1

HCID 3776Isopropanol용매

반응 조건

온도
120 °C

실험 절차

A 800 cm3 autoclave is charged with 16.1 g (0.03 mol) of rosuvastatin n-butylamide, 644 cm3 of water and 43.9 g (63.3 cm3; 0.60 mol) tert-butylamine. The reaction mixture is stirred for 24 hours at 120° C. The mixture is allowed to cool to room temperature, diluted with 2-propanol and evaporated in vacuo. The residue is stirred in the mixture of tert-butylmethylether and heptane (2:5, v/v) and the crystals are filtered. Thus 16.2 g (99%) of rosuvastatin TBA salt are obtained. The crude salt is boiled in acetonitrile/2-propanol (8.6:1, v/v) mixture, subsequently further stirred at room temperature, filtered, washed and dried. The product thus obtained is boiled in acetonitrile, 2-propanol is added to the boiling mixture, decolorized with carbon and filtered. The precipitated crystals are filtered and washed with acetonitrile. Yield 10.9 g (66%) rosuvastatin TBA salt having the purity (as determined by high-performance liquid chromatography, HPLC) exceeds 99.5%.

후처리

  1. temperatureto cool to room temperature
  2. customevaporated in vacuo
  3. stirringThe residue is stirred in the mixture of tert-butylmethylether and heptane (2:5
  4. filtrationv/v) and the crystals are filtered

출처 및 근거

ORD 기록
ord-374a57af9ef0443fb598448c797f88d6
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040696B2

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