Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → t-butyl 4-[6-(N-cyclopentylmethylcarbamoyl)-3-(2-methoxycarbonylvinyl)indol-1-ylmethyl]-3-methoxybenzoate

HRID 1198959Notes

Reaction equation

HRID 1198959 reaction equation
[CH:1]1([CH2:6][NH:7][C:8]([C:10]2[CH:18]=[C:17]3[C:13]([C:14](C=O)=[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.C1(P(=[CH:56][C:57]([O:59][CH3:60])=[O:58])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCOC[CH2:62]1>>[CH:1]1([CH2:6][NH:7][C:8]([C:10]2[CH:18]=[C:17]3[C:13]([C:14]([CH:62]=[CH:56][C:57]([O:59][CH3:60])=[O:58])=[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])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 3

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 312751,4-DioxaneHCID 15013776HCID 15013776, compound

Product 1

HCID 54500983t-butyl 4-[6-(N-cyclopentylmethylcarbamoyl)-3-(2-methoxycarbonylvinyl)indol-1-ylmethyl]-3-methoxybenzoateYield 84%

Procedure

A solution of t-butyl 4-[6-(N-cyclopentylmethylcarbamoyl)-3-formylindol-1-ylmethyl]-3-methoxybenzoate (1.2 g) and methyl (triphenylphosphoranylidene)acetate (1.8 g) in dioxane (12 ml) was heated at reflux for 48 hours. The solvent was evaporated. The resultant residue was purified by flash chromatography on silica gel (600 ml), eluting with 3:7 ethyl acetate:hexane, to give t-butyl 4-[6-(N-cyclopentylmethylcarbamoyl)-3-(2-methoxycarbonylvinyl)indol-1-ylmethyl]-3-methoxybenzoate (1.1 g, 84%) as a yellow solid; mp 163°-164°.

Workup

  1. temperatureat reflux for 48 hours
  2. customThe solvent was evaporated
  3. customThe resultant residue was purified by flash chromatography on silica gel (600 ml)
  4. washeluting with 3:7 ethyl acetate

Sources & evidence

ORD record
ord-4a9070751ca749af8a796669187dc9c4
Source dataset
uspto-grants-1990_02
Patent number
US04898863

Reaction notes

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