Water → Rosuvastatin

HRID 578741

반응식

HRID 578741 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

An autoclave having 800 cm3 volume is charged with 16.1 g (0.03 mol) 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 the temperature of 120° C. The reaction mixture is allowed to cool to room temperature, diluted with 2-propanol and evaporated in vacuo. The residue is stirred in tert-butylmethylether-heptane mixture (2:5, v/v) and the crystals are filtered. Thus 16.2 g (99%) of crude rosuvastatin TBA salt are obtained. The crude salt is boiled in the mixture of acetonitrile and 2-propanol (8.6:1, v/v), stirred at room temperature, filtered, washed and dried. The product thus obtained is suspended in water and tert-butylamine (13 cm3) are added. The mixture is allowed to stand for four days and filtered. The mother lye is allowed to stand for further three days and the precipitated product is filtered, washed and dried. In this way, 4.33 g (25%) Form II rosuvastatin tert-butylammonium salt having the powder X-ray diffractogram of FIG. 1 are obtained.

후처리

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

출처 및 근거

ORD 기록
ord-b10466f342164fc5bed8cf55cc83cfc7
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040696B2

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