Sodium hydride → (S)-2-((tert-butoxycarbonyl)amino)-3-(2-nitrophenoxy)propanoic acid

HRID 464825Notes

Reaction equation

HRID 464825 reaction equation
[H-].[Na+].[C:3]([NH:10][C@H:11]([C:14]([OH:16])=[O:15])[CH2:12][OH:13])([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[H][H].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.O>[N+:26]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[O:13][CH2:12][C@@H:11]([C:14]([OH:16])=[O:15])[NH:10][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])([O-:28])=[O:27]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 738951-Fluoro-2-nitrobenzeneHCID 98766N-[tert-butoxycarbonyl]-L-serineHCID 178418361HCID 178418361, compound

Product 1

HCID 18599736(S)-2-((tert-butoxycarbonyl)amino)-3-(2-nitrophenoxy)propanoic acidYield 75.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

In 200 ml of N,N-dimethylformamide is suspended 10.1 g of 60% sodium hydride (oily), and a solution of 25 g of Boc-L-serine in 10 ml of N,N-dimethylformamide is added dropwise to the suspension in a stream of nitrogen at 0° C. with stirring. After stirring is continued at 0° C. until the evolution of hydrogen stops, 19 g of o-fluoronitrobenzene is added dropwise to the mixture. After the stirring at room temperature for 4 hours, the reaction mixture is poured in ice-cooled water containing dilute hydrochloric acid, followed by extraction with ethyl acetate. The organic layer is washed with water and dried, and then the solvent is evaporated off under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane-ethyl acetate=1:1) to give 30 g of O-(o-nitrophenyl)-Boc-L-serine as a colorless oil.

Workup

  1. stirringAfter stirring
  2. additionthe reaction mixture is poured in ice-
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer is washed with water
  5. customdried
  6. customthe solvent is evaporated off under reduced pressure
  7. customThe resulting residue is purified by silica gel column chromatography (hexane-ethyl acetate=1:1)

Sources & evidence

ORD record
ord-388064bdc8ea4a5e8d62c74005113bd5
Source dataset
uspto-grants-1985_10
Patent number
US04548932

Reaction notes

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