Sodium hydride → HCID 66973497, compound

HRID 1367150Notes

Reaction equation

HRID 1367150 reaction equation
Cl[CH2:2][C:3]([NH:5][C@H:6]([C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[C:11]([F:16])[CH:10]=1)[CH2:7][OH:8])=[O:4].[H-].[Na+].[NH4+].[Cl-]>C1COCC1>[F:16][C:11]1[CH:10]=[C:9]([C@H:6]2[NH:5][C:3](=[O:4])[CH2:2][O:8][CH2:7]2)[CH:14]=[C:13]([F:15])[CH:12]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 66973053HCID 66973053, compound

Product 1

HCID 66973497HCID 66973497, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-chloro-N-[(1R)-1-(3,5-difluorophenyl)-2-hydroxyethyl]acetamide from Step C (840 mg, 3.37 mmol) in THF (75 mL) at 0° C. was added NaH (291 mg of a 60% dispersion in oil, 7.28 mmol) and the mixture was stirred at ambient temperature for 1 h. Saturated aqueous NH4Cl (10 mL) was added and the mixture was extracted with EtOAc (2×20 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—75:25 to 25:75, to give the title compound. MS: m/z=214 (M+1).

Workup

  1. extractionthe mixture was extracted with EtOAc (2×20 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by silica gel chromatography
  6. washeluting with a gradient of hexane

Sources & evidence

ORD record
ord-4a8c7aa39b2f49fd8f430298118431c5
Source dataset
uspto-grants-2011_02
Patent number
US07893079B2

Reaction notes

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