Sodium Carbonate → HCID 90402498, compound

HRID 576716Notes

Reaction equation

HRID 576716 reaction equation
[Cl:1][C:2]1[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:15]=[CH:14][C:3]=1[CH2:4][N:5]1[C@@H:10]([CH3:11])[CH2:9][NH:8][C:7](=[O:12])[C:6]1=[O:13].C(=O)([O-])[O-].[Na+].[Na+].F[B-](F)(F)F.[CH2:33]([O+](CC)CC)[CH3:34]>C(Cl)Cl>[Cl:1][C:2]1[C:17]([C:18]([F:21])([F:19])[F:20])=[CH:16][CH:15]=[CH:14][C:3]=1[CH2:4][N:5]1[C@@H:10]([CH3:11])[CH2:9][N:8]=[C:7]([O:12][CH2:33][CH3:34])[C:6]1=[O:13]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2723982Triethyloxonium tetrafluoroborateHCID 90402638HCID 90402638, compound

Product 1

HCID 90402498HCID 90402498, compoundYield 101.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice cooled solution of Intermediate 4 (1.0 g, 3.1 mmol) and sodium carbonate (6.6 g, 62 mmol) in DCM (45 mL) was added triethyloxonium tetrafluoroborate (1M in DCM, 15.6 mL, 15.6 mmol) dropwise. The ice bath was removed and the reaction was stirred at rt for 1.5 h. Water was added and the mixture was extracted with DCM (×3). The combined organic extracts were dried (Na2SO4), filtered, and concentrated to afford a yellow oil (1.1 g, 99%), which was used directly without further purification.

Workup

  1. customThe ice bath was removed
  2. additionWater was added
  3. extractionthe mixture was extracted with DCM (×3)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-768dfdb6da844b14be50ad234d284591
Source dataset
uspto-grants-2015_05
Patent number
US09040534B2

Reaction notes

Loading…