Ethyl bromoacetate → HCID 67482279, compound

HRID 1191712Notes

Reaction equation

HRID 1191712 reaction equation
COC(=O)C1C=CC(NC(=O)CS[CH:14]2[C:18]([CH3:19])=[C:17]([CH3:20])[C:16](=[O:21])[N:15]2[CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)=NC=1.[H-].[Na+].Br[CH2:36][C:37]([O:39][CH2:40]C)=[O:38].C1C[O:45]CC1>>[CH3:40][O:39][C:37](=[O:38])[CH2:36][O:21][CH:16]1[C:17]([CH3:20])=[C:18]([CH3:19])[C:14](=[O:45])[N:15]1[CH2:22][C:23]1[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=1

Participants

5

Reactant 4

HCID 7748Ethyl bromoacetateHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 16058694HCID 16058694, compound

Product 1

HCID 67482279HCID 67482279, compound

Conditions

Temperature
0 °C

Procedure

The product from Example 1, Part B (400 mg, 1.6 mmol) in 15 mL THF was cooled to 0° C. under N2. Sodium hydride (58 mg, 2.4 mmol) was added in two portions and stirring continued for 0.5 h. Ethyl bromoacetate (400 mg, 2.4 mmol) in 5 mL THF was added dropwise over 5 min, and stirring continued at room temperature for 24 h. Solvent was evaporated, the mixture was cooled to 0° C., EtOAc was added, followed by cold water. The aqueous phase was washed with EtOAc. The combined organics were dried (Na2SO4), filtered, and evaporated. The title compound was isolated as an oil and used without further purification (450 mg, 83%).

Workup

  1. stirringstirring
  2. waitcontinued at room temperature for 24 h
  3. customSolvent was evaporated
  4. additionEtOAc was added
  5. washThe aqueous phase was washed with EtOAc
  6. dry with materialThe combined organics were dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-89fb2aee40c44aefba77c6674e350a5d
Source dataset
uspto-grants-2014_03
Patent number
US08680122B2

Reaction notes

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