Triethylamine → 4-[6-(N-cyclopentylmethylcarbamoyl)-3-(2-methoxycarbonylethyl)indol-1-ylmethyl]-3-methoxybenzoic acid

HRID 1198961Notes

Reaction equation

HRID 1198961 reaction equation
[CH:1]1([CH2:6][NH:7][C:8]([C:10]2[CH:18]=[C:17]3[C:13]([C:14]([CH2:35][CH2:36][C:37]([O:39][CH3:40])=[O:38])=[CH:15][N:16]3[CH2:19][C:20]3[CH:32]=[CH:31][C:23]([C:24]([O:26]C(C)(C)C)=[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(N(CC)CC)C.FC(F)(F)S(O[Si](C)(C)C)(=O)=O>O1CCOCC1.O>[CH:1]1([CH2:6][NH:7][C:8]([C:10]2[CH:18]=[C:17]3[C:13]([C:14]([CH2:35][CH2:36][C:37]([O:39][CH3:40])=[O:38])=[CH:15][N:16]3[CH2:19][C:20]3[CH:32]=[CH:31][C:23]([C:24]([OH:26])=[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

6

Reactant 3

HCID 8471TriethylamineHCID 65367Trimethylsilyl triflateHCID 15013778t-butyl 4-[6-(N-cyclopentylmethylcarbamoyl)-3-(2-methoxycarbonylethyl)indol-1-ylmethyl]-3-methoxybenzoate

Product 1

HCID 150137794-[6-(N-cyclopentylmethylcarbamoyl)-3-(2-methoxycarbonylethyl)indol-1-ylmethyl]-3-methoxybenzoic acidYield 32.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of t-butyl 4-[6-(N-cyclopentylmethylcarbamoyl)-3-(2-methoxycarbonylethyl)indol-1-ylmethyl]-3-methoxybenzoate (1.04 g) in dioxane (6 ml) was treated with triethylamine (0.65 ml) and trimethylsilyl trifluoromethanesulphonate (0.8 ml). The solution was stirred for 24 hours and then was diluted with water to give a viscous oil. The liquids were decanted and the oil was triturated successively with water and hexane. The resultant solid was recrystallized from ethyl acetate/hexane to give 4-[6-(N-cyclopentylmethylcarbamoyl)-3-(2-methoxycarbonylethyl)indol-1-ylmethyl]-3-methoxybenzoic acid (0.3 g, 32%) as an ivory powder; mp 181-182°.

Workup

  1. customto give a viscous oil
  2. customThe liquids were decanted
  3. customthe oil was triturated successively with water and hexane
  4. customThe resultant solid was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-456d08bcd62047679b4f9b1c14696da3
Source dataset
uspto-grants-1990_02
Patent number
US04898863

Reaction notes

Loading…