Methyl iodide → HCID 58392467, 화합물

HRID 561397노트

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HRID 561397 반응식
[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

참가 물질

6

반응물 3

HCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 58392200HCID 58392200, 화합물

생성물 1

HCID 58392467HCID 58392467, 화합물

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매3회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-46f1fef6d3a248adb209ddb82b61724d
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063234B2

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