Hydrochloric Acid → Methyl 4-[5-(2-cyclopentylacetamido)-1-ethylindol-3-ylmethyl]-3-methoxybenzoate

HRID 1904467ノート

反応式

HRID 1904467 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH3:12])[CH:6]=[C:5]2[CH2:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][C:15]=1[O:24][CH3:25].[CH:26]1([CH2:31][C:32](O)=[O:33])[CH2:30][CH2:29][CH2:28][CH2:27]1.Cl.CN(C)CCCN=C=NCC.Cl>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH:26]1([CH2:31][C:32]([NH:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[N:7]([CH2:11][CH3:12])[CH:6]=[C:5]3[CH2:13][C:14]2[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][C:15]=2[O:24][CH3:25])=[O:33])[CH2:30][CH2:29][CH2:28][CH2:27]1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 71606Cyclopentylacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23365902HCID 23365902、化合物

生成物 1

HCID 14626833Methyl 4-[5-(2-cyclopentylacetamido)-1-ethylindol-3-ylmethyl]-3-methoxybenzoate収率 87%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

A mixture of the ester (H) described above (used without further characterization) (4.43 g), cyclopentylacetic acid (1.85 g), 4-(dimethylamino)pyridine (1.76 g), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (3.26 g), was dissolved in methylene chloride (100 ml), under an atmosphere of nitrogen, and stirred at room temperature for 18 hours. The mixture was poured into 1M hydrochloric acid (25 ml), the separated aqueous layer extracted with dichloromethane (2×100 ml), the combined organic extracts washed with water, brine, dried (MgSO4) and evaporated. The residual oil was crystallized from ethanol to give off-white needles which were recrystallized from methylene chloride/hexane to give methyl 4-[5-(2-cyclopentylacetamido)-1-ethylindol-3-ylmethyl]-3-methoxybenzoate (I) as a white powder (5.12 g, 87%); mp 144°-146° C.; partial NMR (250 MHz, DMSO-d6): 1.17(m, 2H), 1.32(t, 3H), 1.4-1.8(m, 6H), 2.25(m, 3H), 3.82(s, 3H, OCH3), 3.92(s, 3H, OCH3), 3.97 (s, 2H, ArCH2), 4.09(q, 2H, CH2CH3), 9.61(s, 1H, NH).

後処理

  1. extractionthe separated aqueous layer extracted with dichloromethane (2×100 ml)
  2. washthe combined organic extracts washed with water, brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residual oil was crystallized from ethanol
  6. customto give off-white needles which
  7. customwere recrystallized from methylene chloride/hexane

出典と根拠

ORDレコード
ord-6d15baa4e911421483a426202ee775ae
出典データセット
uspto-grants-1989_06
特許番号
US04837235

反応ノート

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