Methyl Acrylate → HCID 10691130, compound

HRID 2292775Notes

Reaction equation

HRID 2292775 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]([CH3:18])=[C:5]2[CH2:19][C:20]([NH2:22])=[O:21].[C:23]([O:27][CH3:28])(=[O:26])[CH:24]=[CH2:25]>CO>[CH3:28][O:27][C:23](=[O:26])[CH2:24][CH2:25][NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]([CH3:18])=[C:5]2[CH2:19][C:20]([NH2:22])=[O:21]

Participants

4

Reactant 2

HCID 7294Methyl AcrylateHCID 10732494HCID 10732494, compound

Product 1

HCID 10691130HCID 10691130, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 147 mg (0.5 mmol) of 5-amino-2-methyl-1-(phenylmethyl)-1H-indole-3-acetamide (Example 18) and 2 mL of methyl acrylate in 5 mL of MeOH was stirred for 65 hours, then concentrated at reduced pressure. The residue was chromatographed on silica and eluted with a gradient (EtOAc→5% MeOH/EtOAC) to give a major product and a minor product in the later fractions. The major product was 105 mg (55% yield) of 3-[[3-(2-amino-2-oxoethyl)-2-methyl-1-(phenylmethyl)-1H-indol-5-yl]amino]propanoic acid methyl ester.

Workup

  1. concentrationconcentrated at reduced pressure
  2. customThe residue was chromatographed on silica
  3. washeluted with a gradient (EtOAc→5% MeOH/EtOAC)
  4. customto give a major product

Sources & evidence

ORD record
ord-71bddf925ddc4ff8a768e56701f7ad33
Source dataset
uspto-grants-1997_11
Patent number
US05684034

Reaction notes

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