Sulfuric Acid → Pitavastatin lactone

HRID 445947

反応式

HRID 445947 の反応式
[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

参加物

4

反応物 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

生成物 1

HCID 9801294Pitavastatin lactone収率 50%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-d5ff2873e59945d4b69ddd42d14e0349
出典データセット
uspto-grants-2013_07
特許番号
US08476432B2

関連ノート

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