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

HRID 1596563Notes

Reaction equation

HRID 1596563 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 1 N 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-48ff13c95d544653b85c7c3f03724a47
Source dataset
uspto-grants-2001_09
Patent number
US06291503B1

Reaction notes

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