Ethyl bromoacetate → HCID 86616389, compound

HRID 1866630Notes

Reaction equation

HRID 1866630 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:9]2[NH:14][C:13](=[O:15])[C:12]([CH3:17])([CH3:16])[O:11][CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1.[H-].[Na+].Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].C([O-])(O)=O.[Na+]>CN(C=O)C>[F:8][C:6]1[CH:5]=[C:4]([C@H:9]2[N:14]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:13](=[O:15])[C:12]([CH3:17])([CH3:16])[O:11][CH2:10]2)[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 66973538HCID 66973538, compound

Product 1

HCID 86616389HCID 86616389, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of (5R)-5-(3,5-difluorophenyl)-2,2-dimethylmorpholin-3-one from Step G (150 mg, 0.62 mmol) in DMF (2 mL) at 0° C. was added NaH (27 mg of a 60% dispersion in oil, 0.68 mmol). After 10 min, ethyl bromoacetate (104 mg, 0.62 mmol) was added and the mixture was stirred at 0° C. for 30 min. Saturated aqueous NaHCO3 (5 mL) was added and the mixture was extracted with EtOAc (2×10 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—95:5 to 70:30, to give the title compound. MS: m/z=328 (M+1).

Workup

  1. extractionthe mixture was extracted with EtOAc (2×10 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-82212426f4654d2db799f5120cd83f51
Source dataset
uspto-grants-2009_12
Patent number
US07629338B2

Reaction notes

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