Simvastatin phenylboronate → Simvastatin

HRID 381714

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HRID 381714 반응식
[CH3:1][CH2:2][C:3]([C:6]([O:8][C@@H:9]1[C@@H:14]2[C@@H:15]([CH2:20][CH2:21][C@H:22]3[O:28][C:26](=[O:27])[CH2:25][C@H:24]([OH:29])[CH2:23]3)[C@@H:16]([CH3:19])[CH:17]=[CH:18][C:13]2=[CH:12][C@H:11]([CH3:30])[CH2:10]1)=[O:7])([CH3:5])[CH3:4].C1(B([O-])[O-])C=CC=CC=1>C(O)CCO>[CH3:1][CH2:2][C:3]([C:6]([O:8][C@@H:9]1[C@@H:14]2[C@@H:15]([CH2:20][CH2:21][C@H:22]3[O:28][C:26](=[O:27])[CH2:25][C@H:24]([OH:29])[CH2:23]3)[C@@H:16]([CH3:19])[CH:17]=[CH:18][C:13]2=[CH:12][C@H:11]([CH3:30])[CH2:10]1)=[O:7])([CH3:5])[CH3:4]

참가 물질

3

반응물 1

HCID 86757524Simvastatin phenylboronate

생성물 1

HCID 54454Simvastatin수율 90.1%

시약·촉매·용매 1

HCID 104421,3-Propanediol용매

반응 조건

온도
106 °C

실험 절차

A suspension of simvastatin phenylboronate (30.0 g) and 1,3-propanediol (450 mL) was heated at 105 to 107° C. at 0.2 mm Hg. After 1 hour, 182 mL of distillate was collected and the reaction was cooled to 20 to 25° C. Deionized water (270 mL) was added and toluene (3×75 mL) was used to extract the mixture. The combined toluene layers were washed with water (2×30 mL). The organic solution was heated at reflux for 1 hour and water was azeotropically removed. The solution was concentrated to a final volume of 24 mL under vacuum at 48 to 50° C. To the concentrated solution was added hexanes (215 mL) over 10 minutes. The resulting slurry was cooled to 0 to 5° C. and filtered. The crude simvastatin was washed with 0 to 5° C. hexanes and dried under vacuum to yield 21.0 g (88%) of simvastatin.

후처리

  1. distillation182 mL of distillate was collected
  2. temperaturethe reaction was cooled to 20 to 25° C
  3. additionDeionized water (270 mL) was added
  4. extractionto extract the mixture
  5. washThe combined toluene layers were washed with water (2×30 mL)
  6. temperatureThe organic solution was heated
  7. temperatureat reflux for 1 hour
  8. customwater was azeotropically removed
  9. concentrationThe solution was concentrated to a final volume of 24 mL under vacuum at 48 to 50° C
  10. additionTo the concentrated solution was added hexanes (215 mL) over 10 minutes
  11. temperatureThe resulting slurry was cooled to 0 to 5° C.
  12. filtrationfiltered
  13. washThe crude simvastatin was washed with 0 to 5° C. hexanes
  14. customdried under vacuum

출처 및 근거

ORD 기록
ord-fe2a5176415440fabeb54a35884ccec3
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06307066B1

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