Sodium Hydroxide → HCID 24877453, compound

HRID 1921690Notes

Reaction equation

HRID 1921690 reaction equation
[NH2:1][CH:2]([CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:12]=2)[CH2:7]1)[C:3](O)=[O:4].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C(OCC)(=O)C>[NH2:1][CH:2]([CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:12]=2)[CH2:7]1)[CH2:3][OH:4]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57577379HCID 57577379, compound

Product 1

HCID 24877453HCID 24877453, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

The amino acid 8 prepared in Example 9 was added to a refluxing solution of lithium aluminum hydride (62 mg, 1.63 mmol) in TI-IF (10 ml). The reaction mixture was heated at reflux for 12 hours, subsequently cooled to 0° C. and 10 M NaOH was added and stirred for 20 minutes. Ethyl acetate (20 ml) was added and the mixture was filtered through Celite and magnesium sulfate. The filtrate was concentrated under vacuum and purified by column chromatography (Silica gel, 50% MeOH in CH2Cl2) to provide 41 mg of the product, VPC104059 (21%, two steps).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 12 hours
  3. filtrationthe mixture was filtered through Celite and magnesium sulfate
  4. concentrationThe filtrate was concentrated under vacuum
  5. custompurified by column chromatography (Silica gel, 50% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-7fb4ea6b96e64ee89c72c7479186da40
Source dataset
uspto-grants-2012_05
Patent number
US08173710B2

Reaction notes

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