Lithium hydroxide, monohydrate → 2-Dibenzylamino-3-hydroxy-4-phenyl-butyric acid

HRID 1348618Notes

Reaction equation

C([O:3][C:4](=[O:30])[CH:5]([N:15]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:6]([OH:14])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)C.O.[OH-].[Li+]>O1CCCC1.O>[CH2:23]([N:15]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:5]([CH:6]([OH:14])[CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:4]([OH:30])=[O:3])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To 5.43 g (13.5 mmol) racemic (2S,3R and 2R,3S)-2-dibenzylamino-3-hydroxy-4-phenyl-butyric acid ethyl ester in 75 ml tetrahydrofurane were added 2.28 g (53.8 mmol) lithium hydroxide monohydrate dissolved in 13.5 ml water. The mixture was stirred at 60° C. overnight. Water was added followed by extraction with ethyl acetate. The waterphase was adjusted to pH 1 with 1 N aqueous hydrochloric acid. Extraction with ethylacetate and chromatography on silicagel with dichloromethane/methanol 9/1 yielded 3.50 g (69%) racemic (2S,3R and 2R,3S)-2-dibenzylamino-3-hydroxy-4-phenyl-butyric acid, MS m/e (%): 376.5 (M+H+, 100).

Workup

extractionfollowed by extraction with ethyl acetate
extractionExtraction with ethylacetate and chromatography on silicagel with dichloromethane/methanol 9/1

Sources & evidence

ORD record: ord-7e9f562a86ee41d8b2a2e480d8291d7d
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07211573B2

Reaction notes

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