Trifluoromethanesulfonic anhydride → HCID 46946219, compound
Reaction equation
[C:1]1([CH:7](O)[C:8]([F:11])([F:10])[F:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)CC)(C)C.S(OS(C(F)(F)F)(=O)=O)(C(F)(F)F)(=O)=O.Cl.[C:38]([CH2:40][NH:41][C:42]([C@@H:44]1[CH2:48][C@@H:47]([S:49]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)(=[O:51])=[O:50])[CH2:46][NH:45]1)=[O:43])#[N:39]>ClCCl>[C:38]([CH2:40][NH:41][C:42]([C@@H:44]1[CH2:48][C@@H:47]([S:49]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)(=[O:50])=[O:51])[CH2:46][N:45]1[CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]([F:11])([F:10])[F:9])=[O:43])#[N:39]Participants
Procedure
To a solution of 1-phenyl-2,2,2-trifluoroethanol (0.4 mmole) in dichloromethane (1.4 ml) was added at −50° C. diisopropylethyl amine (2.0 mmole) and triflic anhydride (0.42 mmole) and stirring was continued at −50° for 1 h. To the mixture was added at −50° C. a solution of (2S,4R)-4-benzenesulfonyl-pyrrolidine-2-carboxylic acid cyanomethyl-amide hydrochloride (0.4 mmole) prepared in analogy to experiment K1 in dichloromethane (0.4 ml) and stirring was continued at 22° C. for 2 d. The mixture was partitioned between ethyl acetate and water, the organic layer was dried, evaporated and the residue was chromatographed on silica to give (2S,4R)-4-benzenesulfonyl-1-(2,2,2-trifluoro-1-phenyl-ethyl)-pyrrolidine-2-carboxylic acid cyanomethyl-amide as a colorless solid. MS: 452.1 [M+H]+.
Workup
- stirringstirring
- waitwas continued at 22° C. for 2 d
- customThe mixture was partitioned between ethyl acetate and water
- customthe organic layer was dried
- customevaporated
- customthe residue was chromatographed on silica
Sources & evidence
- ORD record
- ord-6916745f037f4339b3f124786671d835
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08163793B2
Reaction notes
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