1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → Boc-Aib-Trp-NHPh

HRID 1189916Notes

Reaction equation

HRID 1189916 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:39]([NH:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:40])[CH2:29][C:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[NH:32][CH:31]=1>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:39]([NH:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:40])[CH2:29][C:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[NH:32][CH:31]=1)=[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 16735217(S)-2-Amino-3-(1H-indol-3-yl)-N-phenylpropanamide

Product 1

HCID 90045880Boc-Aib-Trp-NHPhYield 65.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.78 g (14.5 mmol) of EDCl was added to 40 ml of THF solution of 1.47 g (7.25 mmol) of Boc-Aib-OH (manufactured by Sigma-Aldrich Corporation), and 2.03 g (7.25 mmol) of H-Trp-NHPh obtained in Synthesis Example 4-2, followed by stirring for 16 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=3/1 to 0/1 (volume ratio)), thereby obtaining 2.20 g of the product with a yield of 65.3%.

Workup

  1. customobtained in Synthesis Example 4-2
  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=3/1 to 0/1 (volume ratio))

Sources & evidence

ORD record
ord-2a5c6a0635984dfc809e2df8ad4e0eee
Source dataset
uspto-grants-2014_03
Patent number
US08674144B2

Reaction notes

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