Citric Acid → HCID 67077094, compound

HRID 1348661Notes

Reaction equation

HRID 1348661 reaction equation
[CH2:1]([N:8]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:9]([CH:13]([OH:16])[CH2:14][CH3:15])[C:10]([OH:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].F[C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=1[N+:34]([O-:36])=[O:35].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O>[CH2:17]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:9]([CH:13]([O:16][C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=1[N+:34]([O-:36])=[O:35])[CH2:14][CH3:15])[C:10]([OH:12])=[O:11])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 24758Sodium hydrideHCID 677672,5-DifluoronitrobenzeneHCID 67077019HCID 67077019, compound

Product 1

HCID 67077094HCID 67077094, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To 14.8 g (47.3 mmol) racemic (2S,3R and 2R,3S)-2-dibenzylamino-3-hydroxy-pentanoic acid in 90 ml dimethylformamide were added at 0° C. 8.26 g (189 mmol) sodium hydride (55%). The suspension was stirred for 2 hours and then 10.4 ml (94.6 mmol) 2,5-difluoro-nitrobenzene in 10 ml dimethylformamide were added. After stirring overnight the mixture was poured under cooling on aqueous 2M citric acid solution. Extraction with ethylacetate and chromatography on silicagel with ethylacetate/heptane (3:7) yielded 12.9 g (61%) racemic (2S,3R and 2R,3S)-2-dibenzylamino-3-(4-fluoro-2-nitro-phenoxy)-pentanoic acid as orange solid, MS m/e (%): 453.0 (M+H+, 100).

Workup

  1. stirringAfter stirring overnight the mixture
  2. additionwas poured
  3. extractionExtraction with ethylacetate and chromatography on silicagel with ethylacetate/heptane (3:7)

Sources & evidence

ORD record
ord-c2e5db75aa334dbaa34eccac3821216a
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Reaction notes

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