Potassium Carbonate → HCID 69931095, compound

HRID 2297702Notes

Reaction equation

HRID 2297702 reaction equation
C(=O)([O-])[O-].[K+].[K+].[ClH:7].Cl.[NH2:9][C@@H:10]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:11]([NH:13][CH2:14][CH2:15][N:16]([CH3:18])[CH3:17])=[O:12].[CH:26](=O)[CH2:27][CH:28]([CH3:30])[CH3:29].C([BH3-])#N.[Na+]>C(O)C.O>[ClH:7].[ClH:7].[CH2:26]([NH:9][C@@H:10]([CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:11]([NH:13][CH2:14][CH2:15][N:16]([CH3:18])[CH3:17])=[O:12])[CH2:27][CH:28]([CH3:30])[CH3:29]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 115523-MethylbutanalHCID 5003444Sodium cyanoborohydrideHCID 69930656HCID 69930656, compound

Product 1

HCID 69931095HCID 69931095, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Anhydrous potassium carbonate (3.32 g) and molecular sieves 3A (5 g) are added successively to a solution of (2S)-2-amino-N1-[2-(dimethylamino)ethyl]-3-phenylpropionamide dihydrochloride (Reference compound No. 8-8, 2.47 g) and isovaleraldehyde (0.69 g) in ethanol (40 ml), and the mixture is stirred at room temperature for two hours. Sodium cyanoborohydride (0.55 g) is further added thereto, and the mixture is stirred at room temperature for two hours. Water is added to the reaction mixture, and the mixture is filtered with Celite. The filtrate is concentrated under reduced pressure, saturated brine is added to the residue, and the whole is extracted with ethyl acetate. The organic layer is washed with a 10% aqueous sodium hydrogencarbonate solution and saturated brine successively, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography, and the resulting oily matter is dissolved in ether (5 ml). A 4.6 N solution of hydrogen chloride in ethyl acetate (4 ml) is added thereto, and the resulting precipitate is filtered off to give 0.40 g (13%) of the titled compound (Reference compound No. 9-1) as crystals.

Workup

  1. filtrationthe mixture is filtered with Celite
  2. concentrationThe filtrate is concentrated under reduced pressure, saturated brine
  3. additionis added to the residue
  4. extractionthe whole is extracted with ethyl acetate
  5. washThe organic layer is washed with a 10% aqueous sodium hydrogencarbonate solution and saturated brine successively
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is purified by silica gel column chromatography
  9. dissolutionthe resulting oily matter is dissolved in ether (5 ml)
  10. additionA 4.6 N solution of hydrogen chloride in ethyl acetate (4 ml) is added
  11. filtrationthe resulting precipitate is filtered off

Sources & evidence

ORD record
ord-6b85e2f4dc614d5ea78b1a9c74ce35fa
Source dataset
uspto-grants-2002_12
Patent number
US06492370B1

Reaction notes

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