Sodium hydride → HCID 21091418, compound

HRID 1348644Notes

Reaction equation

HRID 1348644 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH:13]([OH:16])[CH2:14][CH3:15])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].F[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N+:26]([O-:28])=[O:27]>CN(C)C=O>[C:1]([O:5][C:6]([NH:8][CH:9]([CH:13]([O:16][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N+:26]([O-:28])=[O:27])[CH2:14][CH3:15])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 738951-Fluoro-2-nitrobenzeneHCID 21091419HCID 21091419, compound

Product 1

HCID 21091418HCID 21091418, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

7.05 g (30.2 mmol) 2-tert-Butoxycarbonylamino-3-hydroxy-pentanoic acid in 7 ml dimethylformamide were added at 0° C. to 2.80 g (64.1 mmol) sodium hydride (55%) in 56 ml dimethylformamide. The suspension was stirred for 2 hours and then 3.54 ml (33.2 mmol) 1-fluoro-2-nitrobenzene were added. After stirring for 2 days the mixture was poured on ice/water and extracted with diethylether. The pH was adjusted to 1 by adding aqueous hydrochloric acid. Extraction with ethylacetate and chromatography on silicagel with ethylacetate/heptane 1/1 yielded 6.03 g (56%) 2-tert-butoxycarbonylamino-3-(2-nitro-phenoxy)-pentanoic acid as orange oil, MS m/e (%): 353.4 (M−H, 100).

Workup

  1. stirringAfter stirring for 2 days the mixture
  2. additionwas poured on ice/water
  3. extractionextracted with diethylether
  4. additionby adding aqueous hydrochloric acid
  5. extractionExtraction with ethylacetate and chromatography on silicagel with ethylacetate/heptane 1/1

Sources & evidence

ORD record
ord-5cab52010b8f42178d6805ac1fa78f68
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Reaction notes

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