Water → Methyl 4-[5-(2-carboxy-2-methylpropyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate

HRID 330201Notes

Reaction equation

HRID 330201 reaction equation
FC(F)(F)C(O)=O.[C:8]([C:11]([CH3:40])([CH3:39])[CH:12]([C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[N:19]([CH2:23][CH2:24][CH3:25])[CH:18]=[C:17]2[CH2:26][C:27]1[CH:36]=[CH:35][C:30]([C:31]([O:33][CH3:34])=[O:32])=[CH:29][C:28]=1[O:37][CH3:38])O)([OH:10])=[O:9].C([SiH](CC)CC)C.O>C(Cl)(Cl)(Cl)Cl>[C:8]([C:11]([CH3:39])([CH3:40])[CH2:12][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[N:19]([CH2:23][CH2:24][CH3:25])[CH:18]=[C:17]2[CH2:26][C:27]1[CH:36]=[CH:35][C:30]([C:31]([O:33][CH3:34])=[O:32])=[CH:29][C:28]=1[O:37][CH3:38])([OH:10])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 19870544Methyl 4-[5-(2-carboxy-1-hydroxy-2-methylpropyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate

Product 1

HCID 19870564Methyl 4-[5-(2-carboxy-2-methylpropyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoateYield 56%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Trifluoroacetic acid (1.25 g) was added slowly to a stirred solution of methyl 4-[5-(2-carboxy-1 hydroxy-2-methylpropyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate 0.5 g) and triethylsilane (0.128 g) in carbon tetrachloride (7 ml) under an atmosphere of nitrogen. After 35 min, the mixture was poured into water and extracted with ethyl acetate. The combined organic extracts were washed (water (4 times), brine), dried (MgSO4) and evaporated to give a dark oil. The product was purified by flash chromatography, eluting with 90:10:2 toluene:ethyl acetate:acetic acid, to give methyl 4-[5-(2-carboxy-2-methylpropyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate as an oil (0.27 g, 56%): partial NMR (250 MHz, DMSO-d6): 0.82(t, 3H, CH2CH3), 1.02(s, 6H, C(CH3)2), 1.68(m, 2H, CH2CH3), 291(s, 2H, C(CH3)2CH2), 3.82(s, 3H, OCH3), 3.89(s, 3H, OCH3), 4.01(m, 4H, NCH2, ArCH2Ar'), 12.15(br s, about 1H, COOH).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic extracts were washed (water (4 times), brine)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give a dark oil
  6. customThe product was purified by flash chromatography
  7. washeluting with 90:10:2 toluene

Sources & evidence

ORD record
ord-92804e4c38764e1886b9b2f5de314b36
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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