1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 90045894, compound

HRID 1189914Notes

Reaction equation

HRID 1189914 reaction equation
CCN=C=NCCCN(C)C.Cl.[NH:13]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:14]([C:17]([OH:19])=O)([CH3:16])[CH3:15].[NH2:27][C@H:28]([C:33]([NH:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:34])[CH2:29][CH:30]([CH3:32])[CH3:31]>C1COCC1>[NH:13]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:14]([C:17]([NH:27][C@H:28]([C:33]([NH:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:34])[CH2:29][CH:30]([CH3:32])[CH3:31])=[O:19])([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2733845N-((1,1-dimethylethoxy)carbonyl)-2-methyl-alanineHCID 11031002L-leucine anilide

Product 1

HCID 90045894HCID 90045894, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.76 g (19.6 mmol) of EDCl was added to 40 ml of THF solution of 1.99 g (9.79 mmol) of Boc-Aib-OH (manufactured by Sigma-Aldrich Corporation), and 2.03 g (9.79 mmol) of H-Leu-NHPh obtained in Synthesis Example 2-2, followed by stirring for 17 hours at room temperature. After a reaction mixture was concentrated under reduced pressure, the concentrate was extracted by adding water and ethyl acetate. After an organic layer was washed sequentially with a diluted hydrochloric acid, an aqueous solution of sodium hydrogen carbonate and water (one time for each), it was concentrated under reduced pressure, thereby obtaining crude amide. The obtained amide compound was purified by a silica gel column chromatography (hexane/ethyl acetate=5/1 to 1/1 (volume ratio)), thereby obtaining 2.42 g of the product with a yield of 63.1%.

Workup

  1. customobtained in Synthesis Example 2-2
  2. concentrationAfter a reaction mixture was concentrated under reduced pressure
  3. extractionthe concentrate was extracted
  4. additionby adding water and ethyl acetate
  5. washAfter an organic layer was washed sequentially with a diluted hydrochloric acid
  6. concentrationan aqueous solution of sodium hydrogen carbonate and water (one time for each), it was concentrated under reduced pressure
  7. customobtaining crude amide
  8. customThe obtained amide compound was purified by a silica gel column chromatography (hexane/ethyl acetate=5/1 to 1/1 (volume ratio))

Sources & evidence

ORD record
ord-e6e3b96e45ba44eab055816ef9bc26a6
Source dataset
uspto-grants-2014_03
Patent number
US08674144B2

Reaction notes

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