Methyl iodide → HCID 58392467、化合物

HRID 561397ノート

反応式

HRID 561397 の反応式
[CH:1]([N-]C(C)C)(C)C.[Li+].[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]([C:23]2[C:31]3[C:26](=[C:27]([CH2:32][S:33][CH3:34])[CH:28]=[CH:29][CH:30]=3)[N:25]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH:24]=2)[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:12]([F:42])[CH:11]=1.CI>O1CCCC1.ClCCl>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]([C:23]2[C:31]3[C:26](=[C:27]([CH2:32][S:33][CH3:34])[CH:28]=[CH:29][CH:30]=3)[N:25]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH:24]=2)[CH:17]([CH3:1])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:12]([F:42])[CH:11]=1

参加物

6

反応物 3

HCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 58392200HCID 58392200、化合物

生成物 1

HCID 58392467HCID 58392467、化合物

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒3 回

実験手順

3.55 ml (7.10 mmol) of a 2N solution of lithium diisopropylamide in tetrahydrofuran were introduced into 40 ml of absolute tetrahydrofuran at −78° C., a solution of 3.00 g (5.93 mmol) of the compound from Example 35A in 20 ml of tetrahydrofuran was added, and the mixture was stirred for 1 h. 1.01 g (7.11 mmol) of methyl iodide were added at −78° C., and the reaction mixture was warmed to RT. It was then diluted with dichloromethane, the phases were separated, and the organic phase was washed with 1N hydrochloric acid, dried over magnesium sulfate, filtered and concentrated. The crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in 2.45 g (80% of theory) of the title compound as mixture of diastereomers.

後処理

  1. customthe phases were separated
  2. washthe organic phase was washed with 1N hydrochloric acid
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)

出典と根拠

ORDレコード
ord-46f1fef6d3a248adb209ddb82b61724d
出典データセット
uspto-grants-2011_11
特許番号
US08063234B2

反応ノート

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