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t-butyl 4-[6-(N-cyclopentylmethylcarbamoyl)-3-(2-ethoxycarbonyl-1-propenyl)indol-1-ylmethyl]-3-methoxybenzoate → t-butyl 4-[6-(N-cyclopentylmethylcarbamoyl)-3-(2-ethoxycarbonylpropyl)indol-1-ylmethyl]-3-methoxybenzoate

HRID 1198969
Notes
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Reaction equation

HRID 1198969 reaction equation
[CH:1]1([CH2:6][NH:7][C:8]([C:10]2[CH:18]=[C:17]3[C:13]([C:14]([CH:35]=[C:36]([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH3:37])=[CH:15][N:16]3[CH2:19][C:20]3[CH:32]=[CH:31][C:23]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:22][C:21]=3[O:33][CH3:34])=[CH:12][CH:11]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>CO.[Pd]>[CH:1]1([CH2:6][NH:7][C:8]([C:10]2[CH:18]=[C:17]3[C:13]([C:14]([CH2:35][CH:36]([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH3:37])=[CH:15][N:16]3[CH2:19][C:20]3[CH:32]=[CH:31][C:23]([C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])=[CH:22][C:21]=3[O:33][CH3:34])=[CH:12][CH:11]=2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 53856301t-butyl 4-[6-(N-cyclopentylmethylcarbamoyl)-3-(2-ethoxycarbonyl-1-propenyl)indol-1-ylmethyl]-3-methoxybenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 15013787t-butyl 4-[6-(N-cyclopentylmethylcarbamoyl)-3-(2-ethoxycarbonylpropyl)indol-1-ylmethyl]-3-methoxybenzoateYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst
HCID 887
Methanol
Solvent

Procedure

A solution of t-butyl 4-[6-(N-cyclopentylmethylcarbamoyl)-3-(2-ethoxycarbonyl-1-propenyl) indol-1-ylmethyl]-3-methoxybenzoate (3.3 g) in methanol (30 ml) was treated with 10% (w/w) palladium on carbon (0.8 g) and shaken under 3.45 bars of hydrogen for 18 hours. The catalyst was removed by filtration through diatomaceous earth, and the filtrate was evaporated to give t-butyl 4-[6-(N-cyclopentylmethylcarbamoyl)-3-(2-ethoxycarbonylpropyl)indol-1-ylmethyl]-3-methoxybenzoate (3.3 g, 100%) as a colorless oil: partial NMR (80 MHz, CDCl3) 3.40(t, 2H, NHCH2), 3.94(s, 3H, OCH3), 4.10(q, 2H, OCH2), 5.33(s, 2H, NCH2), 6.14(br t, 1H, NH), 6.63(d, 1H, Ar), 7.04(s, 1H, H2 -indole), 7.85(br s, 1H, H7 indole).

Workup

  1. customThe catalyst was removed by filtration through diatomaceous earth
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-26f308f9469342fcbd3fe204d8a143a0
Source dataset
uspto-grants-1990_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04898863

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes