Sodium Hydroxide → HCID 58909332, compound

HRID 1991556Notes

Reaction equation

HRID 1991556 reaction equation
[OH-].[Na+].BrBr.[CH2:5]([O:12][C:13]1[CH:32]=[CH:31][C:16]([CH2:17][C@H:18]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C@H:19](O)[CH2:20][OH:21])=[CH:15][C:14]=1[F:33])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>O>[CH2:5]([O:12][C:13]1[CH:32]=[CH:31][C:16]([CH2:17][C@H:18]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:29])[CH3:28])[C@H:19]2[CH2:20][O:21]2)=[CH:15][C:14]=1[F:33])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24408BromineHCID 58909337HCID 58909337, compound

Product 1

HCID 58909332HCID 58909332, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To an ice-cold solution of sodium hydroxide (228 mg, 5.7 mmol) in water (2.5 mL) was added bromine (94 μL, 1.84 mmol) dropwise. After stirring for 5 min at 0° C., amide 16 (336 mg, 1.5 mmol) was added in one portion. The reaction mixture was stirred at room temperature for 20 min and then heated at 75° C. for 5 h. The reaction mixture was diluted with water and extracted with methylene chloride. The organic layer was washed with saturated sodium chloride, dried (sodium sulfate), filtered, and concentrated under reduced pressure to give a yellow solid. Purification by flash column chromatography (silica, 95:5 methylene chloride/methanol) gave amine 17 (288 mg, 98%) as a light yellow solid: 1H NMR (300 MHz, CDCl3) δ 7.35 (s, 1H), 2.79 (d, J=7.2 Hz, 2H), 2.08 (m, 1H), 1.13 (m, 1H), 1.06-0.97 (m, 8H).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 20 min
  2. temperatureheated at 75° C. for 5 h
  3. extractionextracted with methylene chloride
  4. washThe organic layer was washed with saturated sodium chloride
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give a yellow solid
  9. customPurification by flash column chromatography (silica, 95:5 methylene chloride/methanol)

Sources & evidence

ORD record
ord-2fe0d98bea054e2cba16d5e143be6a2d
Source dataset
uspto-grants-2010_01
Patent number
US07645780B2

Reaction notes

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