Aniline → HCID 11066741, compound

HRID 1189913Notes

Reaction equation

HRID 1189913 reaction equation
CCN=C=NCCCN(C)C.Cl.[NH:13]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C@H:14]([C:19]([OH:21])=O)[CH2:15][CH:16]([CH3:18])[CH3:17].[NH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C1COCC1>[NH:13]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C@H:14]([C:19]([NH:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:21])[CH2:15][CH:16]([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 6115AnilineHCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 11066741HCID 11066741, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

8.43 g (44.0 mmol) of EDCl was added to 100 ml of THF solution of 9.97 g (40.0 mmol) of Boc-Leu-OH (manufactured by Tokyo Chemical Industry Co., Ltd), 3.65 ml (40.0 mmol) of aniline and 4.60 g (40.0 mmol) of HO-Su(hydroxysuccinimide), followed by stirring for 8 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), the organic layer was dried over sodium sulfate. After the drying agent was separated by filtration, the filtrate was concentrated under reduced pressure, thereby obtaining crude amide. The obtained amide compound was purified by a silica gel column chromatography (hexane/ethyl acetate=9/1 to 2/1 (volume ratio)), thereby obtaining 5.43 g of the product with a yield of 44.3%.

Workup

  1. concentrationAfter a reaction mixture was concentrated under reduced pressure
  2. extractionthe concentrate was extracted
  3. additionby adding water and ethyl acetate
  4. washAfter an organic layer was washed sequentially with a diluted hydrochloric acid
  5. dry with materialan aqueous solution of sodium hydrogen carbonate and water (one time for each), the organic layer was dried over sodium sulfate
  6. customAfter the drying agent was separated by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customobtaining crude amide
  9. customThe obtained amide compound was purified by a silica gel column chromatography (hexane/ethyl acetate=9/1 to 2/1 (volume ratio))

Sources & evidence

ORD record
ord-049b723b6b23494ebd1eaefba96f72ce
Source dataset
uspto-grants-2014_03
Patent number
US08674144B2

Reaction notes

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