Trifluoromethanesulfonic anhydride → HCID 59403460, compound

HRID 1514197Notes

Reaction equation

HRID 1514197 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].O[C:17]1[CH:34]=[CH:33][C:20]2[CH2:21][N:22]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:23][CH2:24][O:25][C:19]=2[CH:18]=1>N1C=CC=CC=1>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][C:17]1[CH:34]=[CH:33][C:20]2[CH2:21][N:22]([C:26]([O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[O:27])[CH2:23][CH2:24][O:25][C:19]=2[CH:18]=1)(=[O:5])=[O:4]

Participants

4

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 59403455HCID 59403455, compound

Product 1

HCID 59403460HCID 59403460, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Trifluoromethanesulfonic anhydride (0.253 ml, 1.498 mmol) was added to an ice cooled solution of 1,1-dimethylethyl 8-hydroxy-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (Preparation 30) (0.265 g, 0.999 mmol) in pyridine (4 ml) and stirred for one hour. The reaction mixture was evaporated, dissolved in 40 ml of EtOAc and washed with 20 ml of 2M HCl and 20 ml of saturated sodium bicarbonate then dried (magnesium sulphate) and evaporated to give the title compound (399 mgs) as a yellow gum. MS (ES) C15H18F3NO6S requires 397; found 298 [M+H−100]+.

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutiondissolved in 40 ml of EtOAc
  3. washwashed with 20 ml of 2M HCl and 20 ml of saturated sodium bicarbonate
  4. dry with materialthen dried (magnesium sulphate)
  5. customevaporated

Sources & evidence

ORD record
ord-bc33a9991a0b4ef5aecdb74727ca9a72
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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