Sulfuric Acid → Pitavastatin lactone

HRID 445947

반응식

HRID 445947 반응식
[CH:1]1([C:4]2[C:13](/[CH:14]=[CH:15]/[C@H:16]3[O:21]C(C)(C)[O:19][C@@H:18]([CH2:24][C:25](N(OC)C)=[O:26])[CH2:17]3)=[C:12]([C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)[CH2:3][CH2:2]1.S(=O)(=O)(O)O>C(#N)C>[CH:1]1([C:4]2[C:13](/[CH:14]=[CH:15]/[C@H:16]3[O:21][C:25](=[O:26])[CH2:24][C@H:18]([OH:19])[CH2:17]3)=[C:12]([C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)[CH2:2][CH2:3]1

참가 물질

4

반응물 2

HCID 1118Sulfuric AcidHCID 86761897E-(6-{2-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]vinyl}-[(4R,6S)-2,2-dimethyl-[1,3]dioxan-4-yl])-N-methoxy-N-methyl-acetamide

생성물 1

HCID 9801294Pitavastatin lactone수율 50%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

E-(6-{2-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]vinyl}-[(4R,6S)-2,2-dimethyl-[1,3]dioxan-4-yl])-N-methoxy-N-methyl-acetamide (3.0 g), acetonitrile (50.0 mL), and sulfuric acid (0.3 mL) were added to a reactor. The reaction mixture was stirred at 50˜60° C. for 5 hours and then concentrated under reduced pressure. Ethyl acetate (50.0 mL) and water (50.0 mL) were added to the resulting residue. The separated organic layer was dried under reduced pressure to obtain E-6-{2-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]vinyl}-(4R,6S)-4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one (1.2 g, yield 50%).

후처리

  1. concentrationconcentrated under reduced pressure
  2. additionEthyl acetate (50.0 mL) and water (50.0 mL) were added to the resulting residue
  3. customThe separated organic layer was dried under reduced pressure

출처 및 근거

ORD 기록
ord-d5ff2873e59945d4b69ddd42d14e0349
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476432B2

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