Trifluoromethanesulfonic anhydride → 1,1-Dimethylethyl 9-{[(trifluoromethyl)sulfonyl]oxy}-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

HRID 1514225Notes

Reaction equation

HRID 1514225 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[C:27]2[O:26][CH2:25][CH2:24][N:23]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:22][C:21]=2[CH:20]=[CH:19][CH:18]=1>N1C=CC=CC=1>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][C:17]1[C:27]2[O:26][CH2:25][CH2:24][N:23]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:22][C:21]=2[CH:20]=[CH:19][CH:18]=1)(=[O:5])=[O:4]

Participants

4

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 59403444tert-butyl 9-hydroxy-2,3-dihydrobenzo[f][1,4]oxazepine-4(5H)-carboxylate

Product 1

HCID 594035221,1-Dimethylethyl 9-{[(trifluoromethyl)sulfonyl]oxy}-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylateYield 95.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

Trifluoromethanesulfonic anhydride (6.04 ml, 35.7 mmol) was added to an ice cooled solution of 1,1-dimethylethyl 9-hydroxy-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (Preparation 62) (6.32 g, 23.82 mmol) in pyridine (100 ml) and stirred at 0° C. for 2 hrs. The pyridine was evaporated and the residue dissolved in EtOAc. Washed with 2M HCl, sat sodium bicarbonate solution, dried over magnesium sulphate and evaporated to give the title compound (9 g) as a yellow oil. MS (ES): C15H18F3NO6S requires 397; found 298 [M+H−100]+.

Workup

  1. customThe pyridine was evaporated
  2. dissolutionthe residue dissolved in EtOAc
  3. washWashed with 2M HCl
  4. dry with materialdried over magnesium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-93f09485a13f4602aae2c2105ba78f00
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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