Triethylamine → HCID 19870621, compound

HRID 330147Notes

Reaction equation

HRID 330147 reaction equation
[CH:1]1([CH2:6][NH:7][C:8]([CH2:10][C:11]2[CH:19]=[C:18]3[C:14]([C:15]([CH2:36][CH2:37][C:38]([O:40][CH3:41])=[O:39])=[CH:16][N:17]3[CH2:20][C:21]3[CH:33]=[CH:32][C:24]([C:25]([O:27]C(C)(C)C)=[O:26])=[CH:23][C:22]=3[O:34][CH3:35])=[CH:13][CH:12]=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]([CH2:10][C:11]2[CH:19]=[C:18]3[C:14]([C:15]([CH2:36][CH2:37][C:38]([O:40][CH3:41])=[O:39])=[CH:16][N:17]3[CH2:20][C:21]3[CH:33]=[CH:32][C:24]([C:25]([OH:27])=[O:26])=[CH:23][C:22]=3[O:34][CH3:35])=[CH:13][CH:12]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 65367Trimethylsilyl triflateHCID 19870604HCID 19870604, compound

Product 1

HCID 19870621HCID 19870621, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of t-butyl 4-[6-(cyclopentylmethylcarbamoyl)methyl-3-(2-methoxycarbonylethyl)indol-1-ylmethyl]-3-methoxybenzoate (0.45 g) in dioxane (3 ml) was treated with triethylamine (0.27 ml) and trimethylsilyl trifluoromethanesulfonate (0.33 ml). The solution was heated at reflux for 30 min and then diluted with water to form a precipitate which was collected by filtration to give 4-[6-(cyclopentylmethycarbamoyl)methyl-3-(2-methoxycarbonylethyl)indol-1-ylmethyl]-3-methoxybenzoic acid (0.40 g, 99%) as a tan powder; partial NMR (80 MHz, CDCl3): 3.66(s, 3H, CO2CH3), 3.70(s, 2H, COCH2Ar) 3.96(s, 3H, OCH3), 5.29(s, 2H, NCH2Ar). (It will be recognized that this compound is also an example of the invention.)

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 30 min
  3. customto form a precipitate which
  4. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-41e928c644494f2ebf223370b2739c73
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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