Water → HCID 86667161, compound

HRID 1753666Notes

Reaction equation

HRID 1753666 reaction equation
[C:1]12([C:11]([O:13][CH2:14][CH2:15][NH:16][S:17]([C:20]([F:23])([F:22])[F:21])(=[O:19])=[O:18])=[O:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.O.[OH-].[Na+].[Br-].[C:28]1([S+:34]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(Cl)(Cl)Cl>[C:1]12([C:11]([O:13][CH2:14][CH2:15][NH:16][S:17]([C:20]([F:23])([F:21])[F:22])(=[O:19])=[O:18])=[O:12])[CH2:2][CH:3]3[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]3)[CH2:8]1)[CH2:10]2.[C:41]1([S+:34]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 11984010Triphenylsulfonium BromideHCID 67954229HCID 67954229, compound

Product 1

HCID 86667161HCID 86667161, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

A 3 L reactor was charged with 240 g (0.63 mol) of the N-[2-(adamantan-1-ylcarbonyloxy)ethyl]trifluoromethanesulfonamide obtained in the above Synthesis Example 1, 800 mL of water and 800 mL of chloroform, and with the temperature inside the reactor maintained at 0° C., 240 g (0.68 mol) of an 11% NaOH solution was gradually added dropwise to the reactor, and the resulting mixture was then stirred for 30 minutes. Subsequently, 244 g (0.71 mol) of triphenylsulfonium bromide was added to the reactor, and the reaction mixture was stirred at room temperature for 15 hours. A phase separation was then performed, and the obtained organic layer was washed 4 times with 800 mL of water and then concentrated under reduced pressure. The resulting yellow oily product was dissolved in acetonitrile and recrystallized in IPE, yielding 360 g of triphenylsulfonium N-[2-(adamantan-1-ylcarbonyloxy)ethyl]trifluoromethanesulfonamide. The purity of the product was 99% and the yield was 87%.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 15 hours
  2. customA phase separation
  3. washthe obtained organic layer was washed 4 times with 800 mL of water
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe resulting yellow oily product was dissolved in acetonitrile
  6. customrecrystallized in IPE

Sources & evidence

ORD record
ord-a651aa7770a64560a43dcae722cda0ed
Source dataset
uspto-grants-2015_10
Patent number
US09164380B2

Reaction notes

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