Hydrochloric Acid → HCID 67076913, compound

HRID 1348584Notes

Reaction equation

HRID 1348584 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][OH:14])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].F[C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1[N+:25]([O-:27])=[O:26].Cl>CN(C)C=O>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][O:14][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1[N+:25]([O-:27])=[O:26])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 677672,5-DifluoronitrobenzeneHCID 98766N-[tert-butoxycarbonyl]-L-serine

Product 1

HCID 67076913HCID 67076913, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

5.00 g (24.4 mmol) (S)-2-tert-Butoxycarbonylamino-3-hydroxy-propionic acid in 5 ml dimethylformamide were added to a suspension of 2.25 g (51.7 mmol) sodium hydride (55%) in 5 ml dimethylformamide at 0° C. The suspension was stirred for 1 hour and then 4.5 ml (26.8 mmol) 2,5-difluoro-nitrobenzene was added. After additional 3 hours of stirring at 0° C. the mixture was poured on ice/water. The ph was adjusted to 1 by adding 7 ml 25% aqueous hydrochloric acid. Extraction with ethylacetate and chromatography on silicagel with ethylacetate/heptane 1:1 yielded 4.35 g (52%) (S)-2-tert-butoxycarbonylamino-3-(4-fluoro-2-nitro-phenoxy)-propionic acid as yellow solid, MS m/e (%): 343.0 (M−H+, 100).

Workup

  1. stirringAfter additional 3 hours of stirring at 0° C. the mixture
  2. additionwas poured on ice/water
  3. extractionExtraction with ethylacetate and chromatography on silicagel with ethylacetate/heptane 1:1

Sources & evidence

ORD record
ord-12459b11c2a1457387a55014b2bc6573
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Reaction notes

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