Hydrochloric Acid → Methyl 4-(5-hexanamido-1-methylindol-3-ylmethyl)-3-methoxybenzoate

HRID 1080761노트

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HRID 1080761 반응식
[C:1](Cl)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[NH2:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15]([CH3:19])[CH:14]=[C:13]2[CH2:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][C:22]=1[O:31][CH3:32].CN1CCOCC1.Cl>ClCCl>[C:1]([NH:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15]([CH3:19])[CH:14]=[C:13]2[CH2:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][C:22]=1[O:31][CH3:32])(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 67340Hexanoyl chlorideHCID 11209537Methyl 4-((5-amino-1-methyl-1H-indol-3-yl)methyl)-3-methoxybenzoate

생성물 1

HCID 23365856Methyl 4-(5-hexanamido-1-methylindol-3-ylmethyl)-3-methoxybenzoate수율 76.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Hexanoylchloride (0.029 g.) was added to a stirred solution of methyl 4-(5-amino-1-methylindol -3-ylmethyl)-3-methoxybenzoate (D) (0.05 g.) and N-methylmorpholine (0.05 g.) in dichloromethane (3 ml.), under an atmosphere of nitrogen. The mixture was stirred for 2 hours and then poured into 1M hydrochloric acid (15 ml.). This mixture was extracted with ethyl acetate (2×20 ml.). The combined extracts were dried (MgSO4), and evaporated. The residual oil was purified by flash chromatography on silica gel (50 ml.), eluting with 4:6 v/v ethyl acetate:hexane, to give a colorless oil, which was crystallized from a mixture of toluene and hexane to give the title compound (0.05 g, 65%) as a white powder; NMR: 0.86(t, 3H, CH2.CH3) 1.28(m 4H, CH2.CH2.CH3), 1.57(quintet 2H, CH2.CH2.CON), 2.25(t,2H, CH2.CH2.CON), 3.69(s,3H, NCH3), 3.82(s,3H, CO.OCH3), 3.92(s,3H, OCH3), 3.9(s, 2H, CH2.Ar), 7.05(s,1H), 7.13(d,1H), 7.27(d,1H), 7.28(d,1H), 7.40(dd,1H), 7.48(s,1H), 7.74(s,1H), 9.61(s,1H).

후처리

  1. extractionThis mixture was extracted with ethyl acetate (2×20 ml.)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. customevaporated
  4. customThe residual oil was purified by flash chromatography on silica gel (50 ml.)
  5. washeluting with 4:6 v/v ethyl acetate
  6. customhexane, to give a colorless oil, which
  7. customwas crystallized from a mixture of toluene and hexane

출처 및 근거

ORD 기록
ord-caa0dff465d84f559868a40d13e2353e
출처 데이터셋
uspto-grants-1996_12
특허 번호
US05583152

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