1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 22611994, compound

HRID 843734Notes

Reaction equation

HRID 843734 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:16])[CH2:5][CH2:6][NH:7][C:8]([CH:10]1[CH2:15][CH2:14][CH2:13][NH:12][CH2:11]1)=[O:9].[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH:27]([CH2:30][CH2:31][C:32](O)=[O:33])[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18].ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C>CN(C)C=O.O>[CH3:2][O:3][C:4](=[O:16])[CH2:5][CH2:6][NH:7][C:8]([CH:10]1[CH2:15][CH2:14][CH2:13][N:12]([C:32](=[O:33])[CH2:31][CH2:30][CH:27]2[CH2:26][CH2:25][N:24]([C:22]([O:21][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:23])[CH2:29][CH2:28]2)[CH2:11]1)=[O:9]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 15125403-(1-((Tert-butoxy)carbonyl)piperidin-4-yl)propanoic acidHCID 70110152HCID 70110152, compound

Product 1

HCID 22611994HCID 22611994, compoundYield 77.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of N-[(3-piperidyl)carbonyl]-β-alanine methyl ester hydrochloride (1.57 g),3-(1-tert-butoxycarbonyl-4-piperidyl)propionic acid (1.61 g) and 1-hydroxybenztriazole (0.96 g) in N,N-dimethylformamide (16 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (1.14 ml) under stirring at 0° C. After stirring at ambient temperature for 1 hour, the mixture was poured into water and extracted with ethyl acetate. The extract was washed with water, brine and dried over MgSO4, and evaporated in vacuo. The residue was purified by chromatography on silica gel eluting with (CHCl3:MeOH 100:1) to give N-[1-{3-(1-tert-butoxycarbonyl-4-piperidyl)propionyl}-3-piperidylcarbonyl]-β-alanine methyl ester as an oil (2.19 g).

Workup

  1. stirringAfter stirring at ambient temperature for 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water, brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. customThe residue was purified by chromatography on silica gel eluting with (CHCl3:MeOH 100:1)

Sources & evidence

ORD record
ord-705457f9ef864d27bb8a5caa507defd0
Source dataset
uspto-grants-2002_04
Patent number
US06380215B1

Reaction notes

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