Hydrochloric Acid → Ethyl 3-(2,4,6-trimethylphenylacetylamino)-3-(3-nitrophenyl)-propionate

HRID 1357066Notes

Reaction equation

HRID 1357066 reaction equation
[C:1]1([CH3:13])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3](C)[C:2]=1[CH2:9][C:10](Cl)=[O:11].[CH:14](N(C(C)C)CC)(C)C.Cl.[NH2:24][CH:25]([C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([N+:38]([O-:40])=[O:39])[CH:33]=1)[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28].Cl>O1CCOCC1.O>[CH3:14][CH:9]([C:2]1[C:1]([CH3:13])=[CH:6][C:5]([CH3:7])=[CH:4][CH:3]=1)[C:10]([NH:24][CH:25]([C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([N+:38]([O-:40])=[O:39])[CH:33]=1)[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[O:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 110307542,4,6-Trimethylbenzeneacetyl chlorideHCID 16188861Ethyl 3-amino-3-(3-nitrophenyl)propanoate hydrochloride

Product 1

HCID 70018979Ethyl 3-(2,4,6-trimethylphenylacetylamino)-3-(3-nitrophenyl)-propionateYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

3.57 g of mesitylacetyl chloride and 5.27 g of diisopropylethylamine were added at 0° C. to a solution of 5.0 g of (1b) in 50 ml of dioxane. The reaction mixture was stirred at 0° C. for 1 h, and was then allowed to warm to room temperature. The solution was added to water and acidified with 1N HCl, extracted with dichloromethane, dried over MgSO4 and concentrated. Chromatographic purification on silica gel (dichloromethane/methanol=20:1) afforded a white solid (yield: 6.0 g).

Workup

  1. temperatureto warm to room temperature
  2. extractionextracted with dichloromethane
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customChromatographic purification on silica gel (dichloromethane/methanol=20:1)

Sources & evidence

ORD record
ord-20f2ce8dd0fe432cbcfc4db1ddce9924
Source dataset
uspto-grants-2003_07
Patent number
US06589972B2

Reaction notes

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