Ethyl Acetate → HCID 15541413, compound

HRID 1861655Notes

Reaction equation

HRID 1861655 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C@@H:8]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]1)=O.C(OCC)(=O)C.[OH-].[Na+]>CCOCC.O1CCCC1>[CH2:18]([C@H:8]([NH2:7])[CH2:9][N:11]1[CH2:12][CH2:13][N:14]([CH3:17])[CH2:15][CH2:16]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 2087046HCID 2087046, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15541413HCID 15541413, compoundYield 89.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (531 mg) was suspended in anhydrous ether (14 ml) with ice cooling in the nitrogen gas atmosphere and then a solution of 1-[(2S)-2-amino-3-phenylpropionyl]-4-methylpiperazine (1.48 g) in anhydrous tetrahydrofuran (7 ml) was dropwise added to the resulting suspension. The reaction system was stirred at room temperature for 4 hours. Ethyl acetate was gradually dropwise added to the reaction liquid with ice cooling till the reaction system did not undergo foaming any more. Then a 2N sodium hydroxide aqueous solution was added to the reaction system and the resulting mixture was extracted with chloroform. The resulting organic phase was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to give the title compound (Reference Compound 1-1, 1.25 g).

Workup

  1. extractionthe resulting mixture was extracted with chloroform
  2. dry with materialThe resulting organic phase was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-487126207af14c889fff1ebc07b7e8f7
Source dataset
uspto-grants-2003_03
Patent number
US06534499B2

Reaction notes

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