Sodium hydride → HCID 56999409, compound

HRID 1722674Notes

Reaction equation

HRID 1722674 reaction equation
[OH:1][CH2:2][C:3]([F:23])([F:22])[C@H:4](O)[C@@H:5]([NH:13][C:14]([O:16]C(C)(C)C)=[O:15])[CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[H-].[Na+]>CN(C=O)C>[CH:7]1([CH2:6][C@H:5]2[C@H:4]([C:3]([F:22])([F:23])[CH2:2][OH:1])[O:16][C:14](=[O:15])[NH:13]2)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 18634371HCID 18634371, compound

Product 1

HCID 56999409HCID 56999409, compoundYield 101.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The resultant compound from Example 70 (596 mg, 1.77 mmol) in dry DMF (15 mL) was added to NaH (260 mg, 6.5 mmol, 60% in oil, hexane washed) in DMF (5 mL) at 0° C. The mixture was stirred at room temperature for 16 hours and the solvent was removed under reduced pressure. The residue was partitioned between ethyl acetate and saturated aqueous NaHCO3 solution and the organic phase was dried over Na2SO4 and evaporated to afford 472 mg (100%) of product as an oil.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and saturated aqueous NaHCO3 solution
  3. dry with materialthe organic phase was dried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-4c981299ebc441b695bb2d7352344352
Source dataset
uspto-grants-1989_08
Patent number
US04857507

Reaction notes

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