Sodium hydride → N-Boc-O-(2-nitrophenyl)-D-serine

HRID 53124Notes

Reaction equation

HRID 53124 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([NH:10][C@@H:11]([C:14]([OH:16])=[O:15])[CH2:12][OH:13])=[O:9])([CH3:6])([CH3:5])[CH3:4].F[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N+:24]([O-:26])=[O:25]>CN(C=O)C>[N+:24]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[O:13][CH2:12][C@H:11]([C:14]([OH:16])=[O:15])[NH:10][C:8]([O:7][C:3]([CH3:6])([CH3:4])[CH3:5])=[O:9])([O-:26])=[O:25]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 738951-Fluoro-2-nitrobenzeneHCID 637603(R)-2-tert-butoxycarbonylamino-3-hydroxy propionic acid

Product 1

HCID 54196434N-Boc-O-(2-nitrophenyl)-D-serine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 1.84 g (0.0768M) of sodium hydride (NaH) in 50 mL of DMF at 0° C. under a nitrogen atmosphere was added dropwise a slurry of 7.39 g (0.0360M) of N-t-butoxycarbonyl-D-serine. After addition was complete, the reaction was warmed to room temperature and stirred for 45 minutes. The reaction was cooled to -5° C. and 4.04 mL (0.0384M) of 2-fluoronitrobenzene was added dropwise. The reaction was then warmed to room temperature and stirred for 1 hour. The reaction was quenched with an equal volume of water and extracted with ethyl acetate. The ethyl acetate extracts were reextracted with water (pH=9). The water layer was then adjusted to pH=7 and extracted with ethyl acetate. The water layer was then adjusted to pH=2 and extracted with ethyl acetate. The pH=2 ethyl acetate extracts were combined, dried, and evaporated to yield 8.98 g of product as an oil.

Workup

  1. additionAfter addition
  2. temperatureThe reaction was cooled to -5° C.
  3. temperatureThe reaction was then warmed to room temperature
  4. stirringstirred for 1 hour
  5. customThe reaction was quenched with an equal volume of water
  6. extractionextracted with ethyl acetate
  7. extractionextracted with ethyl acetate
  8. extractionextracted with ethyl acetate
  9. customdried
  10. customevaporated

Sources & evidence

ORD record
ord-b17446105a5d414897632b90abebcc61
Source dataset
uspto-grants-1997_04
Patent number
US05618808

Reaction notes

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