1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 57042263, compound

HRID 1066574Notes

Reaction equation

HRID 1066574 reaction equation
C([O:5][C:6](=[O:20])[CH2:7][N:8]1[CH2:13][CH2:12][NH:11][C@@H:10]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[C:9]1=[O:19])(C)(C)C.[OH:21][CH:22]([CH2:26][C:27](=[O:40])[N:28]1[CH2:33][CH2:32][N:31]([C:34]2[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=2)[CH2:30][CH2:29]1)[C:23](O)=[O:24].Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O>[OH:21][C@@H:22]([CH2:26][C:27](=[O:40])[N:28]1[CH2:33][CH2:32][N:31]([C:34]2[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=2)[CH2:30][CH2:29]1)[C:23]([N:11]1[CH2:12][CH2:13][N:8]([CH2:7][C:6]([OH:5])=[O:20])[C:9](=[O:19])[C@@H:10]1[CH2:14][C:15]([O:17][CH3:18])=[O:16])=[O:24]

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10636945HCID 10636945, compoundHCID 21200205HCID 21200205, compound

Product 1

HCID 57042263HCID 57042263, compoundYield 16.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of (S)-(3-methoxycarbonylmethyl-2-oxopiperazin-1-yl)acetic acid tert-butyl ester (0.29 g) and 2-hydroxy-4-oxo-4-(4-pyridin-4-ylpiperazin-1-yl)-butanoic acid (0.30 g) in dimethylformamide (15 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.30 g) and the solution was stirred for 24 hours at room temperature. The solution was concentrated to remove dimethylformamide and the residue was purified by means of CHP-20 column chromatography (H2O→30% acetonitrile aqueous solution). To the produced tert-butyl ester derivative (0.20 g) was added trifluoroacetic acid (6 ml) and the solution was stirred for 1 hour at room temperature. The reaction solution was concentrated and the residue was dissolved in water (10 ml), which was purified by means of CHP-20 column chromatography (H2O→5% acetonitrile aqueous solution). The objected fraction was concentrated and subjected to lyophilization to give the titled compound(0.08 g) as a white amorphous powdery product.

Workup

  1. concentrationThe solution was concentrated
  2. customto remove dimethylformamide
  3. customthe residue was purified by means of CHP-20 column chromatography (H2O→30% acetonitrile aqueous solution)
  4. additionTo the produced tert-butyl ester derivative (0.20 g) was added trifluoroacetic acid (6 ml)
  5. stirringthe solution was stirred for 1 hour at room temperature
  6. concentrationThe reaction solution was concentrated
  7. dissolutionthe residue was dissolved in water (10 ml)
  8. customwhich was purified by means of CHP-20 column chromatography (H2O→5% acetonitrile aqueous solution)
  9. concentrationThe objected fraction was concentrated

Sources & evidence

ORD record
ord-0cbe52fb42d6403a868a27f6d2a2644b
Source dataset
uspto-grants-2001_06
Patent number
US06242600B1

Reaction notes

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