Ethyl bromoacetate → HCID 86616391, compound

HRID 1866640Notes

Reaction equation

HRID 1866640 reaction equation
[CH3:1][C@H:2]1[O:7][CH2:6][C@@H:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[NH:4][C:3]1=[O:14].[H-].[Na+].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].C([O-])(O)=O.[Na+]>CN(C=O)C>[CH3:1][C@H:2]1[O:7][CH2:6][C@@H:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:4]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:3]1=[O:14]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 40530436HCID 40530436, compound

Product 1

HCID 86616391HCID 86616391, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of (2R,5R)-2-methyl-5-phenylmorpholin-3-one from Step B (500 mg, 2.62 mmol) in DMF (15 mL) at 0° C. was added NaH (113 mg of a 60% dispersion in oil, 2.83 mmol). After 10 min, ethyl bromoacetate (437 mg, 2.62 mmol) was added and the mixture was stirred at 0° C. for 2 h. Saturated aqueous NaHCO3 (3 mL) was added and the mixture was extracted with EtOAc (2×30 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—90:10 to 60:40, to give the title compound. MS: m/z=278 (M+1).

Workup

  1. extractionthe mixture was extracted with EtOAc (2×30 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-a78e17ef2fb24dd88e29341622fbe835
Source dataset
uspto-grants-2009_12
Patent number
US07629338B2

Reaction notes

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