Acetic Acid → HCID 66811860, compound

HRID 1099590Notes

Reaction equation

HRID 1099590 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][CH:6]([NH2:14])[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)[CH3:2].[CH3:16][CH:17]([CH3:25])[C:18](=O)[CH2:19][C:20]([O:22][CH3:23])=[O:21].C(O)(=O)C.O>C1C=CC=CC=1>[Cl:13][C:10]1[CH:9]=[CH:8][C:7]([CH:6]([NH:14][C:18]([CH:17]([CH3:25])[CH3:16])=[CH:19][C:20]([O:22][CH3:23])=[O:21])[CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:15])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 2759969Methyl 4-methyl-3-oxopentanoateHCID 2847357Ethyl 3-amino-3-(4-chlorophenyl)propanoate

Product 1

HCID 66811860HCID 66811860, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

5.70 g (25.0 mmol) of ethyl-3-amino-3-(4-chlorophenyl)propanoate [V. Wehner et al., Synthesis 14, 2023-2036 (2002)], 3.993 ml (27.5 mmol) of methyl 4-methyl-3-oxopentanoate and 2.87 ml (50.1 mmol) of acetic acid were taken up in 70 ml of benzene and reacted at reflux on a water separator overnight. After cooling, the mixture was washed with saturated aqueous sodium bicarbonate solution, the organic phase was dried with magnesium sulfate and the solvent was destilled off under reduced pressure. This gave 8.57 g (68% of theory) of the target compound in a purity of 70%. The fraction was used without further work-up for the subsequent steps.

Workup

  1. customreacted
  2. temperatureAfter cooling
  3. washthe mixture was washed with saturated aqueous sodium bicarbonate solution
  4. dry with materialthe organic phase was dried with magnesium sulfate

Sources & evidence

ORD record
ord-36320c634acd4e02abe55d01d249b72b
Source dataset
uspto-grants-2012_03
Patent number
US08143411B2

Reaction notes

Loading…