1-Hydroxybenzotriazole → Phenylmethyl 3-oxo-3-[[2-(1-oxopropyl)phenyl]amino]propanoate

HRID 1666680Notes

Reaction equation

HRID 1666680 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:11])[CH2:9][CH3:10].[C:12]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=[O:17])[CH2:13][C:14]([O-])=[O:15].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>O.C1COCC1>[C:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:14](=[O:15])[CH2:13][C:12]([O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:17])(=[O:11])[CH2:9][CH3:10]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 2946511-(2-aminophenyl)propan-1-oneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22247814Benzyl malonate

Product 1

HCID 57970073Phenylmethyl 3-oxo-3-[[2-(1-oxopropyl)phenyl]amino]propanoateYield 17.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 1-(2-aminophenyl)propan-1-one (CAS1196-28-7) (4.6 g), monobenzyl malonate (7.2 g), and THF (46 mL) were added EDC.HCl (7.1 g) and HOBt.H2O (7.1 g), and the mixture was stirred at room temperature for 14 h and then heated to reflux for 8 h. The solvent was evaporated under reduced pressure, and the residue was diluted with ethyl acetate and then washed with saturated aqueous sodium hydrogencarbonate and saturated brine. The organic layer was dried with anhydrous sodium sulfate, the desiccant was removed by filtration, then the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=9:1) to obtain benzyl N-(2-propionylphenyl)malonamate (1.8 g).

Workup

  1. temperatureheated
  2. temperatureto reflux for 8 h
  3. customThe solvent was evaporated under reduced pressure
  4. additionthe residue was diluted with ethyl acetate
  5. washwashed with saturated aqueous sodium hydrogencarbonate and saturated brine
  6. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  7. customthe desiccant was removed by filtration
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=9:1)

Sources & evidence

ORD record
ord-90e8b80d37c444bda2af6d2965cc8478
Source dataset
uspto-grants-2011_10
Patent number
US08044068B2

Reaction notes

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