4-Formylbenzoic acid → 3-[2-(Benzofuran-2-ylmethoxycarbonylamino)-2-(1-phenyl-ethylcarbamoyl)-propyl]-indole-1-carboxylic acid 4-formylbenzoyloxymethyl ester

HRID 1384505Notes

Reaction equation

HRID 1384505 reaction equation
I[CH2:2][O:3][C:4]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH2:15][C:16]([NH:29][C:30]([O:32][CH2:33][C:34]2[O:35][C:36]3[CH:42]=[CH:41][CH:40]=[CH:39][C:37]=3[CH:38]=2)=[O:31])([C:18](=[O:28])[NH:19][CH:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH3:21])[CH3:17])=[CH:7]1)=[O:5].[C:43]([C:46]1[CH:53]=[CH:52][C:49]([CH:50]=[O:51])=[CH:48][CH:47]=1)([OH:45])=[O:44]>C1(C)C=CC=CC=1.[Ag]>[CH:50]([C:49]1[CH:52]=[CH:53][C:46]([C:43]([O:45][CH2:2][O:3][C:4]([N:6]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]([CH2:15][C:16]([NH:29][C:30]([O:32][CH2:33][C:34]3[O:35][C:36]4[CH:42]=[CH:41][CH:40]=[CH:39][C:37]=4[CH:38]=3)=[O:31])([C:18](=[O:28])[NH:19][CH:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH3:21])[CH3:17])=[CH:7]2)=[O:5])=[O:44])=[CH:47][CH:48]=1)=[O:51]

Participants

5

Reactant 2

HCID 120884-Formylbenzoic acidHCID 206699233-[2-(Benzofuran-2-ylmethoxycarbonylamino)-2-(1-phenyl-ethylcarbamoyl)propyl]-indol-1-carboxylic acid iodomethyl ester

Product 1

HCID 206699173-[2-(Benzofuran-2-ylmethoxycarbonylamino)-2-(1-phenyl-ethylcarbamoyl)-propyl]-indole-1-carboxylic acid 4-formylbenzoyloxymethyl esterYield 80.4%

Reagents, catalysts & solvents 2

HCID 23954SilverCatalystHCID 1140TolueneSolvent

Procedure

Compound 7 (1.7 g, 2.5 mmol) and the silver salt of 4-carboxybenzaldehyde (1.29 g, 5.0 mmol) in dry toluene (50 mL) was refluxed for 30 minutes to give a yellow suspension. The solid was removed by filtration through celite, and the solid cake was washed with toluene. The filtrate was concentrated to give a syrup, which was purified by silica gel column eluting with CHCl3 to give compound 19 as a white foam (1.41 g, 80%).

Workup

  1. customto give a yellow suspension
  2. customThe solid was removed by filtration through celite
  3. washthe solid cake was washed with toluene
  4. concentrationThe filtrate was concentrated
  5. customto give a syrup, which
  6. customwas purified by silica gel column
  7. washeluting with CHCl3

Sources & evidence

ORD record
ord-729d1986d0a54499bf598fdba7bd9428
Source dataset
uspto-grants-2001_07
Patent number
US06258800B1

Reaction notes

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