Dicyclohexylcarbodiimide → Ethyl 4-(1,3-dioxoisoindolin-2-YL)-3-oxobutanoate

HRID 711423

反応式

HRID 711423 の反応式
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C:13]([OH:15])=O.[CH3:16][C:17]1(C)[O:22]C(=O)[CH2:20][C:19](=O)[O:18]1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C)C1C=CN=CC=1.ClCCl>[O:11]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2](=[O:1])[N:3]1[CH2:12][C:13](=[O:15])[CH2:16][C:17]([O:18][CH2:19][CH3:20])=[O:22]

参加物

6

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 20825N-Phthaloylglycine

生成物 1

HCID 701239Ethyl 4-(1,3-dioxoisoindolin-2-YL)-3-oxobutanoate収率 85%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 2-(1,3-dioxoisoindolin-2-yl)acetic acid (3.01 g, 14.67 mmol), 2,2-dimethyl-1,3-dioxane-4,6-dione (2.23 g, 15.47 mmol) and 4-dimethylaminopyridine (2.73 g, 22.35 mmol) in dichloromethane (150 mL) was added a solution of DCC (3.36 g, 16.28 mmol) in DCM (50 mL) at 0° C. The mixture was stirred at RT for 16 h. The insoluble materials were filtered off, and the filtrate was washed with 5% NaHSO4 aqueous solution. The organic phase was dried over anhydrous Na2SO4, filtered and the filtrate was concentrated under reduced pressure. The residue was treated with EtOH (200 mL) and the resulting mixture was stirred at 70° C. for 4 h and then concentrated under reduced pressure. Water was added to the residue and the mixture was extracted with EtOAc. The organic layers were washed with water and brine, dried over anhydrous MgSO4, and filtered. The filtrate was concentrated under reduced pressure and the residue was washed with IPE to give the title compound as a colorless solid (3.43 g, 85%). 1H NMR (400 MHz, CDCl3) δ ppm 1.31 (t, J=6.8 Hz, 3H), 3.58 (s, 2H), 4.24 (q, J=6.8 Hz, 2H), 4.67 (s, 2H), 7.73-7.78 (m, 2H), 7.86-7.91 (m, 2H).

後処理

  1. filtrationThe insoluble materials were filtered off
  2. washthe filtrate was washed with 5% NaHSO4 aqueous solution
  3. dry with materialThe organic phase was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. additionThe residue was treated with EtOH (200 mL)
  7. stirringthe resulting mixture was stirred at 70° C. for 4 h
  8. concentrationconcentrated under reduced pressure
  9. additionWater was added to the residue
  10. extractionthe mixture was extracted with EtOAc
  11. washThe organic layers were washed with water and brine
  12. dry with materialdried over anhydrous MgSO4
  13. filtrationfiltered
  14. concentrationThe filtrate was concentrated under reduced pressure
  15. washthe residue was washed with IPE

出典と根拠

ORDレコード
ord-9a0a569ceccd4655a5115e0cc7174145
出典データセット
uspto-grants-2015_11
特許番号
US09181255B2

関連ノート

読み込み中…