1,1'-Carbonyldiimidazole → Methyl 4-[6-(2-cyclopentylacetamido)indol-1-ylmethyl]-3-methoxybenzoate

HRID 1904472노트

반응식

HRID 1904472 반응식
[CH:1]1([CH2:6][C:7]([OH:9])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:22][C:23]1[CH:31]=[C:30]2[C:26]([CH:27]=[CH:28][N:29]2[CH2:32][C:33]2[CH:42]=[CH:41][C:36]([C:37]([O:39][CH3:40])=[O:38])=[CH:35][C:34]=2[O:43][CH3:44])=[CH:25][CH:24]=1>C(Cl)Cl.C(OCC)(=O)C>[CH:1]1([CH2:6][C:7]([NH:22][C:23]2[CH:31]=[C:30]3[C:26]([CH:27]=[CH:28][N:29]3[CH2:32][C:33]3[CH:42]=[CH:41][C:36]([C:37]([O:39][CH3:40])=[O:38])=[CH:35][C:34]=3[O:43][CH3:44])=[CH:25][CH:24]=2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1

참가 물질

6

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 71606Cyclopentylacetic acidHCID 14708762Methyl 4-(6-aminoindol-1-ylmethyl)-3-methoxybenzoate

생성물 1

HCID 19744328Methyl 4-[6-(2-cyclopentylacetamido)indol-1-ylmethyl]-3-methoxybenzoate

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 8857Ethyl Acetate용매

실험 절차

A solution of cyclopentylacetic acid (0.24 ml) and 1,1'-carbonyldiimidazole (0.34 g) in methylene chloride (3 ml) was heated under reflux for 30 minutes and then treated with a solution of ester (B) (0.5 g) in methylene chloride (3 ml). The mixture was heated under reflux for 30 minutes, stirred at room temperature for 24 hours, and then diluted with ethyl acetate. This organic solution was washed sequentially with 10% v/v hydrochloric acid, water, and brine, dried (MgSO4) and evaporated. The residue was purified by flash chromatography on a 6×18 cm silica gel column using 99:1 v/v ethyl acetate:toluene as the eluent followed by recrystallization from hexane/ethyl acetate to give methyl 4-[6-(2-cyclopentylacetamido)indol-1-ylmethyl]-3-methoxybenzoate (P) as a solid; partial NMR: 2.0-2.5(br m, 3H, CH2CH), 3.9(s, 3H, OCH3), 4.0(s, 3H, OCH3), 5.3(s, 2H, NCH2).

후처리

  1. temperatureunder reflux for 30 minutes
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 30 minutes
  4. washThis organic solution was washed sequentially with 10% v/v hydrochloric acid, water, and brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was purified by flash chromatography on a 6×18 cm silica gel column
  8. customtoluene as the eluent followed by recrystallization from hexane/ethyl acetate

출처 및 근거

ORD 기록
ord-370fdd4173bc478f83061eb0575925a1
출처 데이터셋
uspto-grants-1989_06
특허 번호
US04837235

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