Diisopropylamine → HCID 178472193, 화합물

HRID 2075719노트

반응식

HRID 2075719 반응식
N(C(C)C)C(C)C.C([Li])CCC.[CH3:13][CH2:14][O:15][C:16]([CH3:18])=[O:17].[F:19][C:20]([F:30])([F:29])[C:21]([C:23]1[S:27][C:26]([SH:28])=[N:25][CH:24]=1)=[O:22]>C1COCC1>[CH2:14]([O:15][C:16](=[O:17])[CH2:18][C:21]([OH:22])([C:23]1[S:27][C:26]([SH:28])=[N:25][CH:24]=1)[C:20]([F:29])([F:19])[F:30])[CH3:13]

참가 물질

6

반응물 4

HCID 7912DiisopropylamineHCID 8857Ethyl AcetateHCID 178418339ButyllithiumHCID 178519847HCID 178519847, 화합물

생성물 1

HCID 178472193HCID 178472193, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
-78 °C

실험 절차

iPr2NH (205 mg, 2.0 mmol) was dissolved in THF (3.5 mL) and cooled to −10° C. n-Butyllithium (2.5M, 0.81 mL, 2.0 mmol) was added dropwise, and the reaction was cooled to −78° C. EtOAc (179 mg, 2.0 μmmol) in THF (0.5 mL) was added, followed by 10a (188 mg, 0.9 mmol) in THF (10.5 mL), and the reaction was stirred at −78° C. for 1 hour. The reaction was warmed to −10° C. and quenched with 5% aqueous NH4Cl (10 mL). The aqueous layer was extracted with EtOAc, and the combined organic layers were washed with 1N HCl and brine, dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography (50% Et2O in hexanes) to give the desired product, 10b.

후처리

  1. additionwas added dropwise
  2. temperatureThe reaction was warmed to −10° C.
  3. customquenched with 5% aqueous NH4Cl (10 mL)
  4. extractionThe aqueous layer was extracted with EtOAc
  5. washthe combined organic layers were washed with 1N HCl and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel chromatography (50% Et2O in hexanes)

출처 및 근거

ORD 기록
ord-d7eade74771040ea98b580918eabb288
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07919621B2

반응 노트

불러오는 중…