Triethylamine → HCID 57592482, compound

HRID 1784403Notes

Reaction equation

HRID 1784403 reaction equation
Br.[F:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2[C:13]([OH:24])=[CH:14][C:15]3[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17][C:16]=3[CH:23]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.C(N(CC)CC)C.[F:32][C:33]([F:39])([F:38])[S:34](Cl)(=[O:36])=[O:35]>CC(C)=O>[F:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([C:12]2[C:13]([O:24][S:34]([C:33]([F:39])([F:38])[F:32])(=[O:36])=[O:35])=[CH:14][C:15]3[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17][C:16]=3[CH:23]=2)(=[O:11])=[O:10])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 79000Trifluoromethanesulfonyl chlorideHCID 68831940HCID 68831940, compound

Product 1

HCID 57592482HCID 57592482, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To an ice bath cooled solution of D6 (340 mg, 0.82 mmol) in acetone (10 mL) was added triethylamine (0.29 mL, 2.1 mmol) followed by trifluoromethanesulfonyl chloride (0.13 mL, 1.2 mmol). The mixture was stirred at room temperature for 2 hours. The solvent was removed and the residue partitioned between dichloromethane and saturated sodium bicarbonate. The organic layer was removed, dried (MgSO4) and evaporated to yield the title compound D7 as a solid (270 mg). MH+ 468. 1H NMR δ (CDCl3) 2.42 (3H, s), 2.55-2.70 (4H, m), 2.95-3.15 (4H, m), 7.09 (1H, s), 7.15-7.24 (2H, t), 7.93-8.04 (3H, m).

Workup

  1. customThe solvent was removed
  2. customthe residue partitioned between dichloromethane and saturated sodium bicarbonate
  3. customThe organic layer was removed
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-14a3949cfc4c4aacbddb66084abdf429
Source dataset
uspto-grants-2009_03
Patent number
US07504392B2

Reaction notes

Loading…