Methyl Acrylate → HCID 70237628, compound

HRID 2292771Notes

Reaction equation

HRID 2292771 reaction equation
[OH: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([O-])([O-])=O.[K+].[K+].[C:29]([O:33][CH3:34])(=[O:32])[CH:30]=[CH2:31]>CC(C)=O.O>[CH3:34][O:33][C:29](=[O:32])[CH2:30][CH2:31][O: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

6

Reactant 3

HCID 7294Methyl Acrylate2×HCID 11430Potassium CarbonateHCID 10589888HCID 10589888, compound

Product 1

HCID 70237628HCID 70237628, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

5-Hydroxy-2-methyl-1-(phenylmethyl)-1H-indole-3-acetamide (550 mg, 1.8 mmol), 550 mg (4 mmol) of K2CO3 and 0.2 mL of methyl acrylate in 40 mL of acetone was heated to maintain reflux for 100 hours (additional methyl acrylate was added at various times). After cooling, the mixture was diluted with water, extracted with EtOAc, the EtOAc solution washed with saturated NaCl solution and dried (Na2 SO4). After concentrating, the residue was chromatographed on silica (eluted with CH2Cl2 →1% MeOH/CH2Cl2) and crystallized from CH2Cl2 /ether to give 375 mg (55% yield) of 3-[[3-(2-amino-2-oxoethyl)-2-methyl-1-(phenylmethyl)-1H-indol-5-yl]oxy]-propanic acid methyl ester, mp, 113°-115° C.

Workup

  1. temperatureto maintain
  2. temperaturereflux for 100 hours
  3. temperatureAfter cooling
  4. extractionextracted with EtOAc
  5. washthe EtOAc solution washed with saturated NaCl solution
  6. customdried (Na2 SO4)
  7. concentrationAfter concentrating
  8. customthe residue was chromatographed on silica (eluted with CH2Cl2 →1% MeOH/CH2Cl2)
  9. customcrystallized from CH2Cl2 /ether

Sources & evidence

ORD record
ord-811932af1b404671b75e989ff353b909
Source dataset
uspto-grants-1997_11
Patent number
US05684034

Reaction notes

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