Sodium hydride → HCID 86605286, compound

HRID 1348605Notes

Reaction equation

HRID 1348605 reaction equation
[F:1][C:2]([F:25])([F:24])[C@@H:3]([OH:23])[C@@H:4]([C:20]([OH:22])=[O:21])[N:5]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[H-].[Na+].F[C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:30]=1[N+:36]([O-:38])=[O:37]>CN(C)C=O>[CH2:6]([N:5]([CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH:4]([CH:3]([O:23][C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:30]=1[N+:36]([O-:38])=[O:37])[C:2]([F:24])([F:25])[F:1])[C:20]([OH:22])=[O:21])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 677672,5-DifluoronitrobenzeneHCID 67076873HCID 67076873, compound

Product 1

HCID 86605286HCID 86605286, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 15.4 g (43.6 mmol) DL-4,4,4-trifluoro-N,N-bis(phenylmethyl)-threonine in 60 ml dimethylformamide were added in portions 4.03 g (92.4 mmol) sodium hydride (55%) at 0° C. The suspension was stirred for 2 hours and then 10.5 ml (95.9 mmol) 2,5-difluoro-nitrobenzene were added. After stirring overnight at 0° C. the mixture was poured on ice/water. Extraction with ethylacetate and chromatography on silicagel with ethylacetate/heptane 1:1 (and adding 30% methanol after the first five 250 ml fractions) yielded 11.7 g (55%) racemic (2S,3S and 2R,3R)-2-dibenzylamino-4,4,4-trifluoro-3-(4-fluoro-2-nitro-phenoxy)-butyric acid acid as yellow oil, MS m/e (%): 491.1 (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 ethylacetate/heptane 1:1 (and
  4. additionadding 30% methanol after the first five 250 ml fractions)

Sources & evidence

ORD record
ord-d379672ef1124c40ad21b0a7bbf7456d
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Reaction notes

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