Sodium Hydroxide → HCID 57519011, compound

HRID 2109325Notes

Reaction equation

HRID 2109325 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]([N:28]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH3:29])[CH2:22][C:23](OCC)=[O:24])=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>O1CCCC1.O>[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]([N:28]([CH3:29])[C:30](=[O:31])[O:32][C:33]([CH3:34])([CH3:36])[CH3:35])[CH2:22][CH2:23][OH:24])=[CH:17][CH:16]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 57519010HCID 57519010, compound

Product 1

HCID 57519011HCID 57519011, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Tetrahydrofuran (100 ml) was added to lithium aluminum hydride (1.02 g, 27 mmol) under an atmosphere of nitrogen, and a solution of ethyl 3-(4-benzyloxyphenyl)-3-[N-(t-butoxycarbonyl)-N-methylamino]propionate (5.56 g, 13 mmol) obtained from Example 115a in tetrahydrofuran was slowly added thereto at −78° C. After stirring the resulting mixture for 30 minutes, the temperature was gradually raised to 0° C. and then the mixture was stirred for 30 minutes. To the reaction mixture was added sequentially water (1 ml), 15% aqueous sodium hydroxide solution (1 ml) and water (3 ml) and the resulting mixture was stirred at room temperature for 30 minutes. To the mixture was added anhydrous magnesium sulfate and the resulting mixture was filtered. The filtrate was concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column to afford the desired compound (4.78 g).

Workup

  1. customat −78° C
  2. stirringthe mixture was stirred for 30 minutes
  3. stirringthe resulting mixture was stirred at room temperature for 30 minutes
  4. filtrationthe resulting mixture was filtered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-456b866a5d714d2f968f7760adf732f7
Source dataset
uspto-grants-2009_04
Patent number
US07514475B2

Reaction notes

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