Trifluoroacetic acid → HCID 77106012, compound
Reaction equation
FC(F)(F)C(O)=O.[O-]S(C(F)(F)F)(=O)=O.[Bi+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O.[Cl:33][C:34]1[O:38][C:37]([CH:39]=O)=[CH:36][CH:35]=1.[Si]([O:48][CH2:49][CH:50]([SH:72])[CH2:51][N:52]1[C:60]([C:61]2[CH:66]=[CH:65][CH:64]=[C:63]([F:67])[CH:62]=2)=[C:59]2[C:54]([N:55]([CH3:71])[C:56](=[O:70])[N:57]([CH3:69])[C:58]2=[O:68])=[CH:53]1)(C(C)(C)C)(C)C>C1(C)C=CC=CC=1.C(Cl)Cl.[OH-].[Na+]>[Cl:33][C:34]1[O:38][C:37]([CH:39]2[C:53]3=[C:54]4[N:55]([CH3:71])[C:56](=[O:70])[N:57]([CH3:69])[C:58](=[O:68])[C:59]4=[C:60]([C:61]4[CH:66]=[CH:65][CH:64]=[C:63]([F:67])[CH:62]=4)[N:52]3[CH2:51][CH:50]([CH2:49][OH:48])[S:72]2)=[CH:36][CH:35]=1Participants
Procedure
Trifluoroacetic acid (161 μl, 2.094 mmol) was added to a solution of bismuth triflate (41.2 mg, 0.063 mmol), 5-chlorofuran-2-carbaldehyde (30.1 mg, 0.230 mmol) and 6-(3-((tert-butyldimethylsilyl)oxy)-2-mercaptopropyl)-5-(3-fluorophenyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (100 mg, 0.209 mmol) in toluene (2094 μL). The mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with DCM (10 mL) and 1M NaOH(aq) (10 mL). The phases were separated and the aqueous phase was extracted with DCM (3×10 mL). The combined organic extracts were dried over magnesium sulfate and evaporated under vacuum. Purification by chromatography on silica, eluting with 0-50% EtOAc/hexane, afforded the title compound as a mixture of diastereomers.
Workup
- customThe phases were separated
- extractionthe aqueous phase was extracted with DCM (3×10 mL)
- dry with materialThe combined organic extracts were dried over magnesium sulfate
- customevaporated under vacuum
- customPurification by chromatography on silica
- washeluting with 0-50% EtOAc/hexane
Sources & evidence
- ORD record
- ord-dc5d8bd9148d44e0859d976e5e884c86
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09359381B2
Reaction notes
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