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

HRID 1778599ノート

反応式

HRID 1778599 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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)].

後処理

  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)

出典と根拠

ORDレコード
ord-c65f2e37aeba4e3895a218afa919948a
出典データセット
uspto-grants-2016_02
特許番号
US09266908B2

反応ノート

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