1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 66751064, compound

HRID 534988Notes

Reaction equation

HRID 534988 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:21])[C:18]([OH:20])=O)[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].[NH2:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])=[CH:25][CH:24]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C([O-])(O)=O.[Na+]>CN(C)C=O>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:12][CH2:13][N:14]([C:17](=[O:21])[C:18]([NH:22][C:23]2[CH:24]=[CH:25][C:26]([CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])=[CH:27][CH:28]=2)=[O:20])[CH2:15][CH2:16]1)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 417374Methyl 3-(4-aminophenyl)propanoateHCID 516892Sodium BicarbonateHCID 667508542-[4-(2-Tert-butylphenyl)piperazin-1-yl]-2-oxoacetic acid

Product 1

HCID 66751064HCID 66751064, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-[4-(2-tert-butylphenyl)piperazin-1-yl]-2-oxoacetic acid (Example 44, 0.40 g, 1.38 mmol), methyl 3-(4-aminophenyl)propanoate (0.30 g, 1.66 mmol), EDCI (0.26 g, 1.66 mmol) and HOBt (0.25 g, 1.66 mmol) in N,N-dimethylformamide (5 mL) was stirred at room temperature for 4 days. The reaction mixture was poured into saturated NaHCO3 solution and extracted with ethyl acetate. The extract was washed with saturated NaHCO3 solution and brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate 85:15 to 50:50) to give the title compound (0.56 g, 91%) as a white amorphous.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated NaHCO3 solution and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate 85:15 to 50:50)

Sources & evidence

ORD record
ord-dce2873961214fc1b05188cbc1d2f890
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

Loading…