Ethyl bromoacetate → HCID 86616402, compound

HRID 1864899Notes

Reaction equation

HRID 1864899 reaction equation
[O:1]1[CH2:6][C:5](=[O:7])[NH:4][C@@H:3]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[CH2:14][C@H:2]12.[H-].[Na+].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CN(C=O)C>[O:7]=[C:5]1[CH2:6][O:1][C@H:2]2[CH2:14][C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C@H:3]2[N:4]1[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 59445883(4aR,9aS)-4,4a,9,9a-Tetrahydroindeno[2,1-b][1,4]oxazin-3(2H)-onato

Product 1

HCID 86616402HCID 86616402, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (4aR,9aS)-4,4-a,9,9a-tetrahydroindeno[2,1-b][1,4]oxazin-3(2H)-one from Step B (600 mg, 3.17 mmol) in DMF (15 mL) at 0° C. was added NaH (228 mg of a 60% dispersion in oil, 5.71 mmol) and the resulting mixture was stirred for 10 min. Ethyl bromoacetate (0.288 mL, 3.5 mmol) was added and the reaction mixture was stirred for 18 h. The reaction mixture was quenched with saturated aqueous NaHCO3 (10 mL) and then extracted with EtOAc (2×40 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 80:20 to 0:100, to give the title compound. MS: m/z=276 (M+1)

Workup

  1. stirringthe reaction mixture was stirred for 18 h
  2. customThe reaction mixture was quenched with saturated aqueous NaHCO3 (10 mL)
  3. extractionextracted with EtOAc (2×40 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by silica gel chromatography
  8. washeluting with a gradient of hexane:EtOAc 80:20 to 0:100

Sources & evidence

ORD record
ord-1bfe109fc1444fb6b700c174a3b9889a
Source dataset
uspto-grants-2009_12
Patent number
US07625901B2

Reaction notes

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