Acetone → HCID 11469708、化合物

HRID 1766134ノート

反応式

HRID 1766134 の反応式
[CH2:1]([O:3][C:4](=[O:10])/[CH:5]=[CH:6]/[C:7](O)=[O:8])[CH3:2].[C:11]([OH:15])([CH3:14])([CH3:13])[CH3:12].C1CCC(N=C=NC2CCCCC2)CC1.CC(C)=O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:11]([O:15][C:7](=[O:8])/[CH:6]=[CH:5]/[C:4]([O:3][CH2:1][CH3:2])=[O:10])([CH3:14])([CH3:13])[CH3:12]

参加物

7

反応物 4

HCID 180AcetoneHCID 6386tert-ButanolHCID 10868DicyclohexylcarbodiimideHCID 5358902Monoethyl fumarate

生成物 1

HCID 11469708HCID 11469708、化合物収率 35%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of fumaric acid mono-ethyl ester (721 mg, 5 mmol) and tert-butanol (0.938 mL, 10 mmol) in 10 mL of DCM was added DMAP (122 mg, 1 mmol) followed by DCC (2.06 g, 10 mmol). The resulting mixture was stirred at rt for 16 h, taken to dryness under reduced pressure, stirred overnight with 50 mL acetone and filtered to remove DCU. The resulting filtrate was concentrated under reduced pressure, and the residue taken up in EtOAc. The EtOAc was washed twice with 30 mL 0.1 M KHSO4, and once with 30 mL saturated NaHCO3 and once with 30 mL of brine. The resulting EtOAc solution was treated with charcoal and dried over magnesium sulfate, concentrated under reduced pressure, and subjected to silica gel flash chromatography using a gradient of 0–15% EtOAc in hexanes as eluent to give essentially pure (one peak on HPLC) 4-1 (350 mg, 35% yield).

後処理

  1. filtrationfiltered
  2. customto remove DCU
  3. concentrationThe resulting filtrate was concentrated under reduced pressure
  4. washThe EtOAc was washed twice with 30 mL 0.1 M KHSO4
  5. additionThe resulting EtOAc solution was treated with charcoal
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-1c223e4616784300bda6efd59a1b7b2d
出典データセット
uspto-grants-2007_06
特許番号
US07230005B2

反応ノート

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