Acetonitrile → Tenivastatin sodium

HRID 350764

反応式

HRID 350764 の反応式
[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](C)[CH2:10]1)=[O:7])([CH3:5])[CH3:4].[OH-:31].[Na+:32].C(Cl)Cl.[C:36](#N)[CH3:37]>O.CC(C)=O>[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]([OH:28])[CH2:23][C@@H:24]([OH:29])[CH2:25][C:26]([O-:27])=[O:31])[C@@H:16]([CH3:19])[CH:17]=[CH:18][C:13]2=[CH:12][C@H:36]([CH3:37])[CH2:10]1)=[O:7])([CH3:4])[CH3:5].[Na+:32]

参加物

7

反応物 4

HCID 6342Acetonitrile2 回HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 54454Simvastatin

生成物 1

HCID 16760655Tenivastatin sodium収率 77.8%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 962Water溶媒2 回

実験手順

1.43 g (3.42 mmole) of simvastatin lactone was dissolved in 10 mL acetonitrile and treated with water (5 mL) and sodium hydroxide (151 mg, 3.78 mmole). The reaction was stirred at room temperature for 3 days, at which time analytical thin-layer chromatography using 4:1 methylene chloride:acetone eluent indicated essentially complete conversion of the starting lactone to a more polar product. The reaction mixture was then diluted to 50 mL with 1:1 acetonitrile:water, frozen and lyophilized to afford 1.22 g (2.66 mmole, 77.8%) of simvastatin sodium as a fluffy white solid. The 400 MHz 1H nuclear magnetic resonance (NMR) spectrum was consistent with the sodium carboxylate product. 1H NMR (Me2SO-d6) δ 7.6 (br s, 1H), 5.95 (d, 1H), 5.8 (in, 1H), 5.5 (s, 1H), 5.1 (s, 1H), 4.6 (s, 1H), 3.7 (br s, 1H), 3.5 (br s, 1H), 2.3 (m, 2H), 2.2 (d, 1H), 2.0 (m, 2H), 1.8 (m, 2H), 1.6–1.3 (5H), 1.2 (br s, 3H), 1.0 (9H), 0.80 (m, 3H), 0.75 (m, 3H).

出典と根拠

ORDレコード
ord-bd8a76b4229e4c88be97c9e63b294c4e
出典データセット
uspto-grants-2007_02
特許番号
US07183285B2

関連ノート

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