Trifluoromethanesulfonic anhydride → HCID 86753393, compound

HRID 1456365Notes

Reaction equation

HRID 1456365 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].[CH3:16][O:17][CH2:18][C@@H:19]1[O:23][C:22](=[O:24])[N:21]([C:25]2[C:29]3[CH:30]=[CH:31][C:32](O)=[CH:33][C:28]=3[O:27][N:26]=2)[CH2:20]1>N1C=CC=CC=1>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][C:32]1[CH:31]=[CH:30][C:29]2[C:25]([N:21]3[CH2:20][C@H:19]([CH2:18][O:17][CH3:16])[O:23][C:22]3=[O:24])=[N:26][O:27][C:28]=2[CH:33]=1)(=[O:5])=[O:4]

Participants

4

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 135977785HCID 135977785, compound

Product 1

HCID 86753393HCID 86753393, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

8.4 ml (0.050 mol) of trifluoromethanesulphonic anhydride are added at 0° C. over 10 minutes to a solution of 11 g (0.042 mol) of (R)-5-(methoxymethyl)-3-(6-hydroxy-1,2-benzisoxazol-3-yl)oxazolidine-2-one in 110 ml of pyridine. The solution is stirred for 18 hours and then poured into ice-cold 2N aqueous hydrochloric acid solution. The product is extracted with ethyl acetate and then the organic phase is dried over sodium sulphate and concentrated under reduced pressure. 16.5 g of product are obtained.

Workup

  1. extractionThe product is extracted with ethyl acetate
  2. dry with materialthe organic phase is dried over sodium sulphate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ce9e47b6bef84735bd1f354e093fc833
Source dataset
uspto-grants-1998_12
Patent number
US05843975

Reaction notes

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