Hydrochloric Acid → 2-Dibenzylamino-3-(4-fluoro-2-nitro-phenoxy)-4-phenyl-butyric acid

HRID 1348619Notes

Reaction equation

HRID 1348619 reaction equation
[CH2:1]([N:8]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH:9]([CH:13]([OH:21])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:10]([OH:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].F[C:32]1[CH:37]=[CH:36][C:35]([F:38])=[CH:34][C:33]=1[N+:39]([O-:41])=[O:40].Cl>CN(C)C=O>[CH2:22]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:9]([CH:13]([O:21][C:32]1[CH:37]=[CH:36][C:35]([F:38])=[CH:34][C:33]=1[N+:39]([O-:41])=[O:40])[CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:10]([OH:12])=[O:11])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 677672,5-DifluoronitrobenzeneHCID 670768442-Dibenzylamino-3-hydroxy-4-phenyl-butyric acid

Product 1

HCID 670768382-Dibenzylamino-3-(4-fluoro-2-nitro-phenoxy)-4-phenyl-butyric acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

3.50 g (9.32 mmol) racemic (2S,3R and 2R,3S)-2-dibenzylamino-3-hydroxy-4-phenyl-butyric acid in 14 ml dimethylformamide were added at 0° C. to 0.86 g (19.8 mmol) sodium hydride (55%) in 2 ml dimethylformamide. The suspension was stirred for 2 hours and then 2.25 ml (20.5 mmol) 2,5-difluoro-nitrobenzene in 3.4 ml dimethylformamide were added. After stirring overnight at 0° C. the mixture was poured on ice/water. The pH was adjusted to 1 by adding aqueous hydrochloric acid. Extraction with ethylacetate and chromatography on silicagel with dichloromethane/methanol (100:0 to 95:5) yielded 2.95 g (62%) racemic (2S,3R and 2R,3S)-2-dibenzylamino-3-(4-fluoro-2-nitro-phenoxy)-4-phenyl-butyric acid as yellow oil, MS m/e (%): 515.3 (M+H+, 100).

Workup

  1. stirringAfter stirring overnight at 0° C. the mixture
  2. additionwas poured on ice/water
  3. extractionExtraction with ethylacetate and chromatography on silicagel with dichloromethane/methanol (100:0 to 95:5)

Sources & evidence

ORD record
ord-7115e45f01184cda9eec23634948d4cb
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Reaction notes

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