Sodium hydride → HCID 86663881, compound

HRID 1022819Notes

Reaction equation

HRID 1022819 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[O:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10][C@H:9]2[CH2:22][N:23]2[CH2:28][CH2:27][CH2:26][NH:25][C:24]2=[O:29])=[CH:4][C:3]=1[F:30].[H-].[Na+].C1(O[C:40]#[N:41])C=CC=CC=1>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[O:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[CH2:10][C@H:9]2[CH2:22][N:23]2[CH2:28][CH2:27][CH2:26][N:25]([C:40]#[N:41])[C:24]2=[O:29])=[CH:4][C:3]=1[F:30]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 70740Phenyl cyanateHCID 66975082HCID 66975082, compound

Product 1

HCID 86663881HCID 86663881, compoundYield 53.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl (6R,7R)-7-(4-chloro-3-fluorophenyl)-6-[(2-oxotetrahydropyrimidin-1(2H)-yl)methyl]-1,4-oxazepane-4-carboxylate (260 mg) in DMF (2.9 mL) was added sodium hydride (94.0 mg, 60% in oil) under ice-cooling, and the mixture was stirred at 0° C. for 1 hr, and at room temperature for 1 hr. Then, phenyl cyanate (210 mg) was added, and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added distilled water, and the mixture was extracted with ethyl acetate. The obtained extract was washed with distilled water and brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (147 mg).

Workup

  1. temperaturecooling
  2. waitat room temperature for 1 hr
  3. stirringthe mixture was stirred at room temperature for 1 hr
  4. additionTo the reaction mixture was added
  5. distillationdistilled water
  6. extractionthe mixture was extracted with ethyl acetate
  7. extractionThe obtained extract
  8. washwas washed with distilled water and brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customthe solvent was evaporated under reduced pressure
  11. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-9611ce1a71e149e3940fa87901013ea4
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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