Sodium hydride → HCID 67077116, compound

HRID 1348672Notes

Reaction equation

HRID 1348672 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH:11]([OH:31])[CH:12]([N:16]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:13]([OH:15])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].F[C:35]1[CH:40]=[CH:39][C:38]([F:41])=[CH:37][C:36]=1[N+:42]([O-:44])=[O:43]>CN(C)C=O>[CH2:1]([O:8][CH2:9][CH2:10][CH:11]([O:31][C:35]1[CH:40]=[CH:39][C:38]([F:41])=[CH:37][C:36]=1[N+:42]([O-:44])=[O:43])[CH:12]([N:16]([CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:13]([OH:15])=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 677672,5-DifluoronitrobenzeneHCID 67076852HCID 67076852, compound

Product 1

HCID 67077116HCID 67077116, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

6.00 g (14 mmol) racemic (2R,3R and 2S,3S)-5-Benzyloxy-2-dibenzylamino-3-hydroxy-pentanoic acid in 20 ml dimethylformamide were added at 0° C. to a suspension of 1.37 g (31 mmol) sodium hydride (55%) in 25 ml dimethylformamide. The suspension was stirred for 3 hours and then 5.01 g (31 mmol) 2,5-difluoro-nitrobenzene in 10 ml dimethylformamide were added. After stirring overnight the mixture was poured under ice water and the pH was adjusted to 1. Extraction with ethylacetate and chromatography on silicagel with heptane/ethylacetate (4:1 to 1:1) yielded 6.00 g (75%) racemic (2R,3R and 2S,3S)-5-benzyloxy-2-dibenzylamino-3-(4-fluoro-2-nitro-phenoxy)-pentanoic acid as yellow oil, MS m/e (%): 559.3 (M+H+, 100).

Workup

  1. stirringAfter stirring overnight the mixture
  2. additionwas poured under ice water
  3. extractionExtraction with ethylacetate and chromatography on silicagel with heptane/ethylacetate (4:1 to 1:1)

Sources & evidence

ORD record
ord-60a0149e0a5b4dfab2936729f4e8e6b2
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Reaction notes

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