2-Bromoethanol → HCID 136005962, compound

HRID 915929Notes

Reaction equation

HRID 915929 reaction equation
[CH:1]1([C:7]2[C:15]3[C:14](=[O:16])[NH:13][C:12]([C:17]4[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][C:18]=4[O:24][CH3:25])=[N:11][C:10]=3[N:9]([CH3:26])[N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:34][CH2:35][OH:36]>CN(C)C=O>[CH:1]1([C:7]2[C:15]3[C:14](=[O:16])[NH:13][C:12]([C:17]4[CH:22]=[CH:21][C:20]([O:23][CH2:34][CH2:35][OH:36])=[CH:19][C:18]=4[O:24][CH3:25])=[N:11][C:10]=3[N:9]([CH3:26])[N:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 108982-Bromoethanol2×HCID 11430Potassium CarbonateHCID 136005835HCID 136005835, compound

Product 1

HCID 136005962HCID 136005962, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a 5 ml N,N-dimethylformamide solution of 150 mg (0.423 mmol) of the compound obtained in Example 36, 87.7 mg (0.635 mmol) of potassium carbonate and 33 μl (0.466 mmol) of 2-bromoethanol were added. The mixture was stirred at 100° C. for 1 hour and at 120° C. for 2 hours. Further, 16 μl (0.233 mmol) of 2-bromoethanol was added, and the mixture was stirred at 120° C. for 1 hour. Then, the reaction mixture was concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate), and further recrystallized (toluene) to obtain 60 mg (36%) of the captioned compound.

Workup

  1. stirringthe mixture was stirred at 120° C. for 1 hour
  2. concentrationThen, the reaction mixture was concentrated under reduced pressure
  3. additionWater was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe extract was dried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate)
  8. customfurther recrystallized (toluene)

Sources & evidence

ORD record
ord-3d0992f7f04a4e0a97d058f017b679ea
Source dataset
uspto-grants-2007_09
Patent number
US07268128B2

Reaction notes

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