Diisopropylethylamine → 1-[(3-Oxo-2-oxa-bicyclo[2.2.1]heptane-5-carbonyl)-amino]-2-vinyl-cyclo-propane carboxylic acid ethyl ester

HRID 390112ノート

反応式

HRID 390112 の反応式
[O:1]=[C:2]1[CH:7]2[CH2:8][CH:4]([CH2:5][CH:6]2[C:9]([OH:11])=O)[O:3]1.[CH2:12]([O:14][C:15]([C:17]1([NH2:22])[CH2:19][CH:18]1[CH:20]=[CH2:21])=[O:16])[CH3:13].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[CH2:12]([O:14][C:15]([C:17]1([NH:22][C:9]([CH:6]2[CH2:5][CH:4]3[CH2:8][CH:7]2[C:2](=[O:1])[O:3]3)=[O:11])[CH2:19][CH:18]1[CH:20]=[CH2:21])=[O:16])[CH3:13]

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22082824Ethyl 1-amino-2-vinylcyclopropanecarboxylateHCID 462449653-Oxo-2-oxabicyclo[2.2.1]heptane-5-carboxylic acid

生成物 1

HCID 668704341-[(3-Oxo-2-oxa-bicyclo[2.2.1]heptane-5-carbonyl)-amino]-2-vinyl-cyclo-propane carboxylic acid ethyl ester収率 99.2%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 3-oxo-2-oxa-bicyclo[2.2.1]heptane-5-carboxylic acid (857 mg, 5.5 mmol), in DMF (14 ml) and DCM (25 ml) at room temperature, was added 1-amino-2-vinylcyclopropanecarboxylic acid ethyl ester (1.15 g, 6.0 mmol), HATU (2.29 g, 6.0 mmol) and DIPEA (3.82 ml, 22 mmol). The reaction was stirred under N2-atmosphere at ambient temperature for 1 h. LC/MS analysis showed complete conversion and the reaction mixture was concentrated in vacuo. The residue was re-dissolved in DCM (100 ml) and 0.1 M HCl (aq) and the layers separated. The organic phase was washed with NaHCO3 (aq) and brine, dried (MgSO4) and filtered. Removal of the solvent in vacuo afforded the title compound (1.6 g, 99%). LC/MS (Method A): tR=2.46 min, >95%, m/z (ESI+)=294(MH+)

後処理

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. dissolutionThe residue was re-dissolved in DCM (100 ml)
  3. custom0.1 M HCl (aq) and the layers separated
  4. washThe organic phase was washed with NaHCO3 (aq) and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customRemoval of the solvent in vacuo

出典と根拠

ORDレコード
ord-57689a36e03349d38db96e39d0d76196
出典データセット
uspto-grants-2013_02
特許番号
US08383584B2

反応ノート

読み込み中…