Dimethylformamide → HCID 86699865, compound

HRID 1772118Notes

Reaction equation

HRID 1772118 reaction equation
[Br:1][C:2]1[C:3]([CH2:22][OH:23])=[C:4]([NH:8][CH2:9][C:10]2[CH:14]=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[S:12][C:11]=2[C:19](O)=[O:20])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.CN(C=O)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>O>[Br:1][C:2]1[C:3]([CH2:22][OH:23])=[C:4]([N:8]2[C:19](=[O:20])[C:11]3[S:12][C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:14][C:10]=3[CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 86699863HCID 86699863, compound

Product 1

HCID 86699865HCID 86699865, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 50-mL single-neck round-bottomed flask equipped with a magnetic stirrer was purged with nitrogen and charged with 114f (540 mg, 1.36 mmol), triethylamine (275 mg, 2.72 mmol) and anhydrous DMF (10 mL). Benzotriazol-1-yl-oxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP, 782 mg, 1.77 mmol) was added, and the reaction was stirred at room temperature for 16 h. After this time, the reaction was diluted with water (20 mL), and the resulting suspension was filtered. The filter cake was dissolved in methylene chloride (40 mL), and the solution was washed with saturated aqueous sodium bicarbonate (10 mL), and water (10 mL), and dried over sodium sulfate. The drying agent was removed by filtration, and the solvent was evaporated under reduced pressure. The resulting residue was purified by flash chromatography to afford a 60% yield of 114g (305 mg) as a white solid: mp 55-56° C.; 1H NMR (500 MHz, CDCl3) δ 7.65 (d, 1H, J=8.0 Hz), 7.25 (m, 1H), 7.20 (d, 1H, J=8.0 Hz), 6.89 (s, 1H), 4.68 (s, 2H), 4.66 (s, 2H), 1.46 (s, 9H).

Workup

  1. customA 50-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. customwas purged with nitrogen
  3. filtrationthe resulting suspension was filtered
  4. dissolutionThe filter cake was dissolved in methylene chloride (40 mL)
  5. washthe solution was washed with saturated aqueous sodium bicarbonate (10 mL), and water (10 mL)
  6. dry with materialdried over sodium sulfate
  7. customThe drying agent was removed by filtration
  8. customthe solvent was evaporated under reduced pressure
  9. customThe resulting residue was purified by flash chromatography

Sources & evidence

ORD record
ord-fd03488a196e467f9321e99fc6164c3d
Source dataset
uspto-grants-2016_02
Patent number
US09249123B2

Reaction notes

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