Sodium hydride → HCID 40530436, compound

HRID 1864841Notes

Reaction equation

HRID 1864841 reaction equation
Cl[CH:2]([CH3:15])[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>[CH3:15][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]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 66973554HCID 66973554, compound

Product 1

HCID 40530436HCID 40530436, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-chloro-N-[(1R)-2-hydroxy-1-phenylethyl]propanamide from Step A (1.30 g, 5.71 mmol) in THF (100 mL) at 0° C. was added NaH (493 mg of a 60% dispersion in oil, 12.3 mmol) and the mixture was stirred at ambient temperature for 18 h. Saturated aqueous NaHCO3 (10 mL) was added and the mixture was extracted with EtOAc (3×20 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 0:100, to give the title compound. MS: m/z=192 (M+1).

Workup

  1. extractionthe mixture was extracted with EtOAc (3×20 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-16676b83a36a4ec783d3ab81aeefb4f0
Source dataset
uspto-grants-2009_12
Patent number
US07625901B2

Reaction notes

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