Potassium Hydroxide → 2-Dibenzylamino-3-hydroxy-3-methyl-butyric acid

HRID 1348639

Reaction equation

C([O:3][C:4](=[O:25])[CH:5]([N:10]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]([OH:9])([CH3:8])[CH3:7])C.[OH-].[K+].P([O-])(O)(O)=O.[Na+]>CO.O>[CH2:18]([N:10]([CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH:5]([C:6]([OH:9])([CH3:8])[CH3:7])[C:4]([OH:25])=[O:3])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To 2.90 g (8.49 mmol) 2-dibenzylamino-3-hydroxy-3-methyl-butyric acid ethyl ester in 300 ml methanol were added 3.21 g (51.0 mmol) potassium hydroxide dissolved in 100 ml water. The mixture was stirred at 60° C. overnight. 500 ml saturated, aqueous sodium dihydrogenphosphate solution were added followed by extraction with ethyl acetate. Chromatography on silicagel with ethylacetate/heptan (50:50 to 100:0) yielded 1.41 g (53%) 2-dibenzylamino-3-hydroxy-3-methyl-butyric acid, MS m/e (%): 312.3 (M−H, 100).

Workup

extractionfollowed by extraction with ethyl acetate

Sources & evidence

ORD record: ord-3b4b424094904dfaac8d044f39af4af2
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07211573B2

Linked notes

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