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

HRID 515958

반응식

HRID 515958 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e9dc617c7bfb493681438194a1883e98
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108970B2

연결된 노트

불러오는 중…