Sodium hydride → HCID 86731201, compound

HRID 2277146Notes

Reaction equation

HRID 2277146 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].[OH:12][CH2:13][C@@H:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH3:15].[H-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[NH2:7][C:6]1[CH:8]=[C:2]([CH:3]=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10])[O:12][CH2:13][C@@H:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH3:15]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 753995-Fluoro-2-nitroanilineHCID 70231031,1-Dimethylethyl N-((1S)-2-hydroxy-1-methylethyl)carbamate

Product 1

HCID 86731201HCID 86731201, compoundYield 43.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-fluoro-2-nitroaniline (2.00 g) and tert-butyl ((2S)-1-hydroxypropan-2-yl)carbamate (2.25 g) in DMF (50 mL) was added sodium hydride (60% in oil, 0.564 g), and the mixture was stirred at room temperature for 10 min. The reaction mixture was diluted with ethyl acetate, and washed with saturated brine. The obtained organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (1.75 g).

Workup

  1. washwashed with saturated brine
  2. dry with materialThe obtained organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-b7188a6f300146578e80b3fbd4aef780
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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