N,N-Dimethylethylenediamine → HCID 59923450, compound

HRID 2297719Notes

Reaction equation

HRID 2297719 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH2:5].[OH:7][CH2:8][CH2:9][N:10]([CH2:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:11](=[O:33])[NH:12][C@@H:13]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=1)[C:14](OC1C=CC=CC=1)=[O:15]>O1CCCC1>[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH:5][C:14](=[O:15])[C@@H:13]([NH:12][C:11]([N:10]([CH2:9][CH2:8][OH:7])[CH2:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33])[CH2:23][C:24]1[CH:25]=[CH:26][C:27]([N+:30]([O-:32])=[O:31])=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 86586958HCID 86586958, compound

Product 1

HCID 59923450HCID 59923450, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-(dimethylamino)ethylamine (362 mg) in tetrahydrofuran (3 ml) is added to a solution of phenyl (2S)-2-[3-(2-hydroxyethyl)-3-phenethylureido]-3-(4-nitrophenyl)propionate (Compound No. 1-35, 392 mg) in tetrahydrofuran (5 ml) under ice cooling, and the mixture is stirred at room temperature for 1.5 hours. The reaction mixture is concentrated under reduced pressure, water is added to the concentrate, and the whole is extracted with ethyl acetate. The organic layer is washed with water and saturated brine successively, dried over andhydrous sodium sulfate and concentrated under reduced pressure. The resulting oily matter is purified by silica gel column chromatography to give 314 mg (81%) of the titled compound (Compound No. 19-1).

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure, water
  2. additionis added to the concentrate
  3. extractionthe whole is extracted with ethyl acetate
  4. washThe organic layer is washed with water and saturated brine successively
  5. dry with materialdried over andhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting oily matter is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e7c210339ba742d3801b94fad57cf9ce
Source dataset
uspto-grants-2002_12
Patent number
US06492370B1

Reaction notes

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