Perfluorobutanesulfonic anhydride → Tert-Butyl (S)-2-(Nonafluorobutane-1-Sulphonyloxy)Propionate

HRID 1510985Notes

Reaction equation

[F:1][C:2]([F:26])([C:22]([F:25])([F:24])[F:23])[C:3]([F:21])([F:20])[C:4]([F:19])([F:18])[S:5]([O:8][CH:9]([CH3:17])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])(=[O:7])=[O:6].FC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(OS(C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)(=O)=O)(=O)=O>>[F:26][C:2]([F:1])([C:22]([F:23])([F:24])[F:25])[C:3]([F:21])([F:20])[C:4]([F:19])([F:18])[S:5]([O:8][C@@H:9]([CH3:17])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])(=[O:7])=[O:6]

Participants

Reactant 2

HCID 4281883Perfluorobutanesulfonic anhydride

HCID 86648205Tert-butyl nonafluorobutanesulphonyloxypropionate

Product 1

HCID 86648204Tert-Butyl (S)-2-(Nonafluorobutane-1-Sulphonyloxy)PropionateYield 82%

Procedure

The production of tert-butyl nonafluorobutanesulphonyloxypropionate was effected with nonafluorobutanesulphonic anhydride as in example 1 with a yield of 82% (ee>99%).

Sources & evidence

ORD record: ord-765fe335c0434d17bb4415b6d3eac2a4
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08212065B2

Reaction notes

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