Phenylalanine anilide → HCID 90045798, compound

HRID 1189918Notes

Reaction equation

HRID 1189918 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:36]([NH:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:37])[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH: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:36]([NH:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:37])[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:19])([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 151952Phenylalanine anilideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2733845N-((1,1-dimethylethoxy)carbonyl)-2-methyl-alanine

Product 1

HCID 90045798HCID 90045798, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.04 g (22.1 mmol) of EDCl was added to 60 ml of THF solution of 2.99 g (14.7 mmol) of Boc-Aib-OH (manufactured by Sigma-Aldrich Corporation), and 3.53 g (14.7 mmol) of H-Phe-NHPh obtained in Synthesis Example 6-2, 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 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 5.79 g of the product with a yield of 92.6%.

Workup

  1. customobtained in Synthesis Example 6-2
  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-c332a340758f40d2a2435756734a280d
Source dataset
uspto-grants-2014_03
Patent number
US08674144B2

Reaction notes

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