Methyl 4-aminobenzoate → Methyl 4-{[5-methoxy-1-(5-methoxy-3-methyl-1-benzofuran-2-yl)pentyl]amino}benzoate

HRID 2091242노트

반응식

HRID 2091242 반응식
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([C:9]1[O:10][C:11]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:12]=2[C:13]=1[CH3:14])=O.[NH2:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=1.C(=O)([O-])O.[Na+].C([BH3-])#N.[Na+]>C(Cl)Cl.O1CCCC1.[Ti](Cl)(Cl)(Cl)Cl.C(O)(=O)C.C(N(CC)CC)C>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]([NH:21][C:22]1[CH:23]=[CH:24][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:30][CH:31]=1)[C:9]1[O:10][C:11]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:12]=2[C:13]=1[CH3:14]

참가 물질

10

반응물 4

HCID 12082Methyl 4-aminobenzoateHCID 516892Sodium Bicarbonate2회HCID 5003444Sodium cyanoborohydrideHCID 667785075-Methoxy-1-(5-methoxy-3-methyl-1-benzofuran-2-yl)pentan-1-one

생성물 1

HCID 66778149Methyl 4-{[5-methoxy-1-(5-methoxy-3-methyl-1-benzofuran-2-yl)pentyl]amino}benzoate수율 90.2%

시약·촉매·용매 5

HCID 24193Titanium Tetrachloride촉매HCID 176Acetic Acid용매HCID 6344Dichloromethane용매2회HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매

실험 절차

To a mixture of 5-methoxy-1-(5-methoxy-3-methyl-1-benzofuran-2-yl)pentan-1-one (797 mg) synthesized above, methyl 4-aminobenzoate (479 mg), triethylamine (3.21 mL) and methylene chloride (10 mL) was added a 1.0M solution (3.46 mL) of titanium (IV) chloride in methylene chloride at 0° C., and the mixture was stirred under argon atmosphere at room temperature for 3.5 days. Saturated aqueous sodium hydrogen carbonate solution was added to quench the reaction, and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to give a dark brown oil. To a solution (10 mL) of the obtained oil in tetrahydrofuran were added acetic acid (824 μL) and sodium cyanoborohydride (362 mg), and the mixture was stirred at room temperature for 1 hr. Saturated aqueous sodium hydrogen carbonate solution was added to quench the reaction, and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (0-40% ethyl acetate/hexane) to give the title object compound (1.07 g, 90%) as a brown oil.

후처리

  1. customto quench
  2. customthe reaction
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give a dark brown oil
  8. stirringthe mixture was stirred at room temperature for 1 hr
  9. customto quench
  10. customthe reaction
  11. extractionthe reaction mixture was extracted with ethyl acetate
  12. washThe extract was washed with saturated brine
  13. dry with materialdried over magnesium sulfate
  14. concentrationconcentrated under reduced pressure
  15. customThe residue was purified by silica gel column chromatography (0-40% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-a642531a30294046a4919a4c8ec073e2
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08436043B2

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