Ethyl 3-(triphenyl-lambda~5~-phosphanylidene)propanoate → t-butyl 4-[6-(N-cyclopentylmethylcarbamoyl)-3-(2-ethoxycarbonyl-1-propenyl)indol-1-ylmethyl]-3-methoxybenzoate

HRID 1198968Notes

Reaction equation

HRID 1198968 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]=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.[C:37]([CH2:42][CH:43]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:39][CH2:40][CH3:41])=[O:38]>O1CCOCC1>[CH:1]1([CH2:6][NH:7][C:8]([C:10]2[CH:18]=[C:17]3[C:13]([C:14]([CH:35]=[C:42]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH3:43])=[CH:15][N:16]3[CH2:19][C:20]3[CH:32]=[CH:31][C:23]([C:24]([O:26][C:27]([CH3:30])([CH3:28])[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

Participants

4

Reactant 2

HCID 12607919Ethyl 3-(triphenyl-lambda~5~-phosphanylidene)propanoateHCID 15013776HCID 15013776, compound

Product 1

HCID 53856301t-butyl 4-[6-(N-cyclopentylmethylcarbamoyl)-3-(2-ethoxycarbonyl-1-propenyl)indol-1-ylmethyl]-3-methoxybenzoateYield 100.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of t-butyl 4-[6-(N-cyclopentylmethylcarbamoyl)-3-formylindol-1-ylmethyl]3-methoxybenzoate (Example 1, part(f)) (2.8 g) and (carbethoxyethylidene)triphenylphosphorane (4.6 g) in dioxane (29 ml) was heated at reflux for 18 hours. The solvent was evaporated. The resultant residue was purified by flash chromatography on silica gel (192 ml), eluting with 1:4 ethyl acetate:hexane to give t-butyl 4-[6-(N-cyclopentylmethylcarbamoyl)-3-(2-ethoxycarbonyl-1-propenyl)indol-1-ylmethyl]-3-methoxybenzoate (3.3 g, 100%) as a light yellow solid; mp 118°-120°; NMR (80 MHz, CDCl3) 2.15(d, 3H, CCH3), 3.40(dd, 2H, NHCH2), 5.42(s, 2H, NCH2), 6.22(br t, 1H, NH), 6.78(d, 1H, Ar).

Workup

  1. temperatureat reflux for 18 hours
  2. customThe solvent was evaporated
  3. customThe resultant residue was purified by flash chromatography on silica gel (192 ml)
  4. washeluting with 1:4 ethyl acetate

Sources & evidence

ORD record
ord-2bc86316e88e4a7b8a84a7484aef4554
Source dataset
uspto-grants-1990_02
Patent number
US04898863

Reaction notes

Loading…