2,2,2-Trifluoroethanol → 2-acetamido-N-tert-butyl-2-(3-(4-chlorobenzyl)-3-formamidocyclobutyl)hex-5-enamide

HRID 1778599노트

반응식

HRID 1778599 반응식
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][C:7]2([NH:17][CH:18]=[O:19])[CH2:10][CH:9]([C:11](=O)[CH2:12][CH2:13][CH:14]=[CH2:15])[CH2:8]2)=[CH:4][CH:3]=1.[C:22]([O-:25])(=O)[CH3:23].[NH4+:26].[C:27]([N+:31]#[C-])([CH3:30])([CH3:29])[CH3:28].FC(F)(F)[CH2:35][OH:36]>C(OCC)(=O)C>[C:22]([NH:26][C:11]([CH:9]1[CH2:10][C:7]([CH2:6][C:5]2[CH:20]=[CH:21][C:2]([Cl:1])=[CH:3][CH:4]=2)([NH:17][CH:18]=[O:19])[CH2:8]1)([CH2:12][CH2:13][CH:14]=[CH2:15])[C:35]([NH:31][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:36])(=[O:25])[CH3:23]

참가 물질

6

반응물 4

HCID 64092,2,2-TrifluoroethanolHCID 23577Tert-Butyl isocyanideHCID 517165Ammonium AcetateHCID 89514331N-(1-(4-chlorobenzyl)-3-pent-4-enoylcyclobutyl)formamide

생성물 1

HCID 895143752-acetamido-N-tert-butyl-2-(3-(4-chlorobenzyl)-3-formamidocyclobutyl)hex-5-enamide수율 45%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

A solution of N-(1-(4-chlorobenzyl)-3-pent-4-enoylcyclobutyl)formamide (0.5 g, 1.64 mmol) and ammonium acetate (1.14 g, 9.84 mmol) in 2,2,2-trifluoroethanol (4 mL). was treated with tert-butyl isocyanide (1.1 mL, 9.84 mmol) and stirred at room temperature for 3 days. Once complete, the solution was diluted with ethyl acetate (15 mL) and quenched with 2M HCl (10 mL). After stirring vigorously for 1 h, the phases were separated and the organic layer was washed with water and saturated aqueous sodium chloride, dried over MgSO4, filtered and concentrated. Purification by column chromatography (gradient 25-75% ethyl acetate in heptane) afforded the subject compound as a colorless oil (330, mg, 45% yield). ESI MS found for C24H34ClN3O3 m/z [448.6 (M+1), 470.6 (M+Na+), 446.3 (M−1)].

후처리

  1. customquenched with 2M HCl (10 mL)
  2. stirringAfter stirring vigorously for 1 h
  3. customthe phases were separated
  4. washthe organic layer was washed with water and saturated aqueous sodium chloride
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by column chromatography (gradient 25-75% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-c65f2e37aeba4e3895a218afa919948a
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09266908B2

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