1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86757988, compound

HRID 843737Notes

Reaction equation

HRID 843737 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:38])[C@@H:6]([NH2:37])[CH2:7][NH:8][C:9]([C@@H:11]1[CH2:16][CH2:15][CH2:14][N:13]([C:17](=[O:36])[CH2:18][CH2:19][CH:20]2[CH2:25][CH2:24][N:23]([C:26]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:27])[CH2:22][CH2:21]2)[CH2:12]1)=[O:10])[CH3:3].[CH3:39][O:40][CH2:41][CH2:42][C:43](O)=[O:44].ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C>CN(C)C=O.O>[CH2:2]([O:4][C:5](=[O:38])[C@@H:6]([NH:37][C:43](=[O:44])[CH2:42][CH2:41][O:40][CH3:39])[CH2:7][NH:8][C:9]([C@@H:11]1[CH2:16][CH2:15][CH2:14][N:13]([C:17](=[O:36])[CH2:18][CH2:19][CH:20]2[CH2:21][CH2:22][N:23]([C:26]([O:28][CH2:29][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)=[O:27])[CH2:24][CH2:25]2)[CH2:12]1)=[O:10])[CH3:3]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 1344423-Methoxypropionic acidHCID 86584070HCID 86584070, compound

Product 1

HCID 86757988HCID 86757988, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of N-[(R)-1-{3-(1-benzyloxycarbonyl-4-piperidyl)propionyl}-3-piperidylcarbonyl]-2(S)-amino-β-alanine ethyl ester hydrochloride (1 g), 3-methoxypropionic acid (0.17 ml) and 1-hydroxybenztriazole (0.24 g) in N,N-dimethylformamide (10 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (0.33 ml) under stirring at 0° C. After stirring at ambient temperature for overnight, the mixture was poured into water and extracted with ethyl acetate. The extract washed with water, brine and dried over MgSO4, and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with (CHCl3:MeOH=100:1) to give N-[(R)-1-{3-(1-benzyloxycarbonyl-4-piperidyl)propionyl}-3-piperidylcarbonyl]-2(S)-(3-methoxypropionyl)amino-β-alanine ethyl ester (0.59 g) as an oil.

Workup

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

Sources & evidence

ORD record
ord-97ea019b21e74bae9d13d7c6d532af8e
Source dataset
uspto-grants-2002_04
Patent number
US06380215B1

Reaction notes

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