Sodium hydride → HCID 66973517, compound

HRID 1864854Notes

Reaction equation

HRID 1864854 reaction equation
Cl[CH:2]([CH2:15][CH3:16])[C:3]([NH:5][C@H:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:7][OH:8])=[O:4].[H-].[Na+].C([O-])(O)=O.[Na+]>C1COCC1>[CH2:15]([C@H:2]1[O:8][CH2:7][C@@H:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:5][C:3]1=[O:4])[CH3:16]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 66973514HCID 66973514, compound

Product 1

HCID 66973517HCID 66973517, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-chloro-N-[(1R)-2-hydroxy-1-phenylethyl]butanamide from Step A (2.75 g, 11.4 mmol) in THF (200 mL) at 0° C. was added NaH (983 mg of a 60% dispersion in oil, 24.6 mmol) and the mixture was stirred at ambient temperature for 18 h. Saturated aqueous NaHCO3 (20 mL) was added and the mixture was extracted with EtOAc (3×40 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 0:100, to give the title compound. MS: m/z=206 (M+1).

Workup

  1. extractionthe mixture was extracted with EtOAc (3×40 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-7fbf230c16c94409bb1719b667b0119b
Source dataset
uspto-grants-2009_12
Patent number
US07625901B2

Reaction notes

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