Hydrochloric Acid → HCID 67077050, compound

HRID 1348630Notes

Reaction equation

HRID 1348630 reaction equation
[CH:1]1([CH:4]([OH:24])[CH:5]([N:9]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:6]([OH:8])=[O:7])[CH2:3][CH2:2]1.[H-].[Na+].F[C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=1[N+:35]([O-:37])=[O:36].Cl>CN(C)C=O>[CH:1]1([CH:4]([O:24][C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=2[N+:35]([O-:37])=[O:36])[CH:5]([N:9]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:6]([OH:8])=[O:7])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 677672,5-DifluoronitrobenzeneHCID 67077070HCID 67077070, compound

Product 1

HCID 67077050HCID 67077050, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

1.30 g (4.00 mmol) racemic (2R,3S and 2S,3R)-3-Cyclopropyl-2-dibenzylamino-3-hydroxy-propionic acid in 4 ml dimethylformamide were added at 0° C. to 0.37 g (8.48 mmol) sodium hydride (55%) in 4 ml dimethylformamide. The suspension was stirred for 2 hours and then 0.96 ml (8.8 mmol) 2,5-difluoro-nitrobenzene in 3.4 ml dimethylformamide were added. After stirring overnight 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 diethylether/heptane (25:75 to 100:0) yielded 1.57 g (85%) racemic (2R,3S and 2S,3R)-3-cyclopropyl-2-dibenzylamino-3-(4-fluoro-2-nitro-phenoxy)-propionic acid as light yellow foam, MS m/e (%): 465.0 (M+H+, 100).

Workup

  1. stirringAfter stirring overnight the mixture
  2. additionwas poured on ice/water
  3. extractionExtraction with ethylacetate and chromatography on silicagel with diethylether/heptane (25:75 to 100:0)

Sources & evidence

ORD record
ord-5cea972b41574d3c82a81028b8827dad
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Reaction notes

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