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

HRID 2091005노트

반응식

HRID 2091005 반응식
[CH3:1][CH:2]([CH3:16])[CH2:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[C:10]=1[CH3:11])=O.[NH2:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=1.C(=O)([O-])O.[Na+].C([BH3-])#N.[Na+]>[Ti](Cl)(Cl)(Cl)Cl.O1CCCC1.CO.C(O)(=O)C.ClCCl.C(N(CC)CC)C>[CH3:1][CH:2]([CH3:16])[CH2:3][CH:4]([NH:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:26][CH:27]=1)[C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[C:10]=1[CH3:11]

참가 물질

11

반응물 4

HCID 12082Methyl 4-aminobenzoateHCID 516892Sodium Bicarbonate2회HCID 5003444Sodium cyanoborohydrideHCID 667790263-Methyl-1-(3-methyl-1-benzofuran-2-yl)butan-1-one

생성물 1

HCID 66777907Methyl 4-{[3-methyl-1-(3-methyl-1-benzofuran-2-yl)butyl]amino}benzoate수율 78.2%

시약·촉매·용매 6

HCID 24193Titanium Tetrachloride촉매HCID 176Acetic Acid용매HCID 887Methanol용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매

실험 절차

To a mixture of 3-methyl-1-(3-methyl-1-benzofuran-2-yl)butan-1-one (200 mg) synthesized above, methyl 4-aminobenzoate (140 mg), triethylamine (1.03 mL) and dichloromethane (5 mL) was added titanium (IV) chloride (122 μL) at 0° C., and the mixture was stirred at room temperature overnight. Saturated aqueous sodium hydrogen carbonate solution was added to quench the reaction, and the 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 solid. To a mixture of the obtained solid, acetic acid (1 mL), methanol (5 mL) and tetrahydrofuran (5 mL) was added sodium cyanoborohydride (175 mg) by small portions, 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 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 (ethyl acetate:hexane=1:4, volume ratio) to give the title object compound (254 mg, 78%) as a pale-yellow solid.

후처리

  1. customto quench
  2. customthe reaction
  3. extractionthe 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 solid
  8. stirringthe mixture was stirred at room temperature for 1 hr
  9. customto quench
  10. customthe reaction
  11. extractionthe 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 (ethyl acetate:hexane=1:4, volume ratio)

출처 및 근거

ORD 기록
ord-0aa6010598684d46ae3eba3a3c24b707
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08436043B2

반응 노트

불러오는 중…