1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86588493, compound

HRID 1862532Notes

Reaction equation

HRID 1862532 reaction equation
Cl.[CH2:2]([O:9][C:10](=[O:26])[C@@H:11]([NH:22][C:23](=[O:25])[CH3:24])[CH2:12][NH:13][C:14]([C@@H:16]1[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]1)=[O:15])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[N:27]1[CH:32]=[CH:31][C:30]([CH:33]=[CH:34][C:35](O)=[O:36])=[CH:29][CH:28]=1.ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C>CN(C)C=O>[CH2:2]([O:9][C:10](=[O:26])[C@@H:11]([NH:22][C:23](=[O:25])[CH3:24])[CH2:12][NH:13][C:14]([C@@H:16]1[CH2:21][CH2:20][CH2:19][N:18]([C:35](=[O:36])[CH:34]=[CH:33][C:30]2[CH:31]=[CH:32][N:27]=[CH:28][CH:29]=2)[CH2:17]1)=[O:15])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 953033-(4-Pyridinyl)-2-propenoic acidHCID 86588489HCID 86588489, compound

Product 1

HCID 86588493HCID 86588493, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-[(R)-3-piperidylcarbonyl]-2(S)-acetylamino-β-alanine benzyl ester hydrochloride (231 mg), 3-(4-pyridyl)-2-propenoic acid (82 mg) and 1-hydroxybenzotriazole (81 mg) in dimethylformamide (2 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (0.11 ml) at 0° C. The mixture was stirred for 2 hours at room temperature, then poured into ice water-ethyl acetate. The separated organic layer was washed with water, aqueous saturated NaHCO3, brine, dried over Na2SO4, and evaporated in vacuo. The residue was purified by silica gel chromatography eluting with CHCl3—MeOH (96:4) to give N-[(R)-1-[3-(4-pyridyl)-2-propenoyl]-3-piperidylcarbonyl]-2(S)-acetylamino-β-alanine benzyl ester (263 mg) as a colorless oil.

Workup

  1. washThe separated organic layer was washed with water, aqueous saturated NaHCO3, brine
  2. dry with materialdried over Na2SO4
  3. customevaporated in vacuo
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with CHCl3—MeOH (96:4)

Sources & evidence

ORD record
ord-9d9991f13e654b22a0e938864a320bb1
Source dataset
uspto-grants-2003_03
Patent number
US06538007B1

Reaction notes

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