Dimethylformamide → HCID 82677013, compound

HRID 2405653Notes

Reaction equation

HRID 2405653 reaction equation
C([N:4]([CH2:8][CH3:9])[CH:5]([CH3:7])C)(C)C.IC[C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19]C)=[CH:14][CH:13]=1.S([O-])([O-])(=O)=[O:22].[Mg+2].CN([CH:30]=[O:31])C>>[CH2:14]([C:15]1[CH:18]=[CH:19][C:9]([CH2:8][NH:4][CH2:5][C:7]([O:31][CH3:30])=[O:22])=[CH:17][CH:16]=1)[CH2:13][CH3:12]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 81531DiisopropylethylamineHCID 86690145HCID 86690145, compound

Product 1

HCID 82677013HCID 82677013, compoundYield 77%

Procedure

Under argon condition, glycine methyl ether (448 mg, 3.57 mmol) was dissolved in 5 mL of dry DMF and then N,N-diisopropylethylamine (DIPEA; 777 μL, 4.46 mmol) and 1-(iodomethyl)-4-propylbenzene (232 mg, 0.892 mmol) were added. The reaction mixture was then stirred for one day at room temperature. Upon completion of the reaction, the reaction was terminated by adding 10 mL of water and the reaction mixture was extracted with diethyl ether (10 mL×4). The organic layer thus obtained was treated with anhydrous magnesium sulfate to remove water. The precipitate was filtered out and the resulting solution was concentrated by distillation under reduced pressure and purified by column chromatography to obtain 152 mg (0.687 mmol, 77%) of the desired compound.

Workup

  1. customUpon completion of the reaction
  2. customthe reaction was terminated
  3. additionby adding 10 mL of water
  4. extractionthe reaction mixture was extracted with diethyl ether (10 mL×4)
  5. customThe organic layer thus obtained
  6. customto remove water
  7. filtrationThe precipitate was filtered out
  8. concentrationthe resulting solution was concentrated by distillation under reduced pressure
  9. custompurified by column chromatography

Sources & evidence

ORD record
ord-2cc6d6f0652d4787948acaa31b6ce525
Source dataset
uspto-grants-2014_08
Patent number
US08809012B2

Reaction notes

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