Trifluoromethylsulfonamide → HCID 57925961, compound

HRID 1013458Notes

Reaction equation

HRID 1013458 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][P:5]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)(=[O:8])[CH2:4][CH2:3]1.[F:16][C:17]([F:23])([F:22])[S:18](N)(=[O:20])=[O:19]>CN(C=O)C>[F:16][C:17]([F:23])([F:22])[S:18]([O:15][C:12]1[CH:13]=[CH:14][C:9]([P:5]2(=[O:8])[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)=[CH:10][CH:11]=1)(=[O:20])=[O:19]

Participants

4

Reactant 2

HCID 79001TrifluoromethylsulfonamideHCID 57925832HCID 57925832, compound

Product 1

HCID 57925961HCID 57925961, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(1-Methyl-4-oxido-1,4-azaphosphinan-4-yl)phenol (0.50 g, 2.22 mmol) was made 0.5 M in DMF and N-Phenyl-bis(trifluorometanesulfonamide (1.19 g, 3.33 mmol) was added, followed by TEA (0.62 mL, 4.44 mmol). The mixture was stirred at ambient temperature for 16 h then the precipitate was filtered off and the filtrate was concentrated in vacuo. The residue was purified by HPLC (20-95% MeCN in water w/0.025% TFA). Pure fractions were identified, combined and concentrated in vacuo. The residue was taken up in EtOAc and washed with saturated aqueous sodium bicarbonate (1×) then dried (MgSO4) and concentrated in vacuo to afford the requisite product as a freebase. MS: cal'd 358 (MH+), exp 358 (MH

Workup

  1. filtrationthe precipitate was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by HPLC (20-95% MeCN in water w/0.025% TFA)
  4. concentrationconcentrated in vacuo
  5. washwashed with saturated aqueous sodium bicarbonate (1×)
  6. dry with materialthen dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto afford the requisite product as a freebase

Sources & evidence

ORD record
ord-385f3c369d0145a5b575ad599404b297
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

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