Aniline → HCID 15228170, compound

HRID 1189917Notes

Reaction equation

HRID 1189917 reaction equation
CCN=C=NCCCN(C)C.Cl.[NH:13]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C@H:14]([C:22]([OH:24])=O)[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[NH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C1COCC1>[NH:13]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C@H:14]([C:22]([NH:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:24])[CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 15228170HCID 15228170, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7.67 g (40.0 mmol) of EDCl was added to 106 ml of THF solution of 5.31 g (20.0 mmol) of Boc-Phe-OH (manufactured by Tokyo Chemical Industry Co., Ltd), 1.82 ml (20.0 mmol) of aniline and 3.06 g (20.0 mmol) of HO-Bt, followed by stirring for 6 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 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 (toluene/ethyl acetate=9/1 to 7/1 (volume ratio)), thereby obtaining 5.93 g of the product with a yield of 87.1%.

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 an aqueous solution of sodium hydrogen carbonate and water (one time for each), the organic layer
  5. dry with materialwas 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 (toluene/ethyl acetate=9/1 to 7/1 (volume ratio))

Sources & evidence

ORD record
ord-d491234c98be4e18ae46afc6cf576ade
Source dataset
uspto-grants-2014_03
Patent number
US08674144B2

Reaction notes

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