Diisopropylamine → HCID 178458806, 화합물

HRID 2075717노트

반응식

HRID 2075717 반응식
N(C(C)C)C(C)C.C([Li])CCC.[S:13]1[CH:17]=[CH:16][N:15]=[C:14]1[SH:18].[F:19][C:20]([F:26])([F:25])[C:21](=[O:24])[CH2:22][CH3:23]>C1COCC1>[F:19][C:20]([F:26])([F:25])[C:21]([C:17]1[S:13][C:14]([SH:18])=[N:15][CH:16]=1)([OH:24])[CH2:22][CH3:23]

참가 물질

6

반응물 4

HCID 7912DiisopropylamineHCID 2382881,1,1-Trifluorobutan-2-oneHCID 178418339ButyllithiumHCID 178527881HCID 178527881, 화합물

생성물 1

HCID 178458806HCID 178458806, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

iPr2NH (2.0 g, 19.9 mmol) was dissolved in THF (23 mL) and cooled to −78° C. n-Butyllithium (2.5M, 8.0 mL, 19.9 mmol) was added dropwise, followed by thiazole-2-thiol (0.9 g, 7.9 mmol) in THF (5 mL). After 10 minutes, trifluoro-2-butanone (0.5 g, 4.0 mmol) was added and the reaction was stirred at −78° C. for 6 hours. The reaction was warmed to room temperature and quenched with 5% aqueous NH4Cl (20 mL). The aqueous layer was acidified and extracted with EtOAc, and the combined organic layers were dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography (50% EtOAc in hexanes) to give the desired product, 10b.

후처리

  1. additionwas added dropwise
  2. temperatureThe reaction was warmed to room temperature
  3. customquenched with 5% aqueous NH4Cl (20 mL)
  4. extractionextracted with EtOAc
  5. dry with materialthe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography (50% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-336bc8768f0a4388b092edd8a08237d4
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07919621B2

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