Ethyl Acetate → HCID 16731845, compound
Reaction equation
[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([N:11]2[C@H:15]([C:16]([F:19])([F:18])[F:17])[C@@H:14]3[C@H:20]([O:23][Si](C(C)(C)C)(C)C)[CH2:21][CH2:22][N:13]3[C:12]2=[O:31])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Cl-].[NH4+].CCOC(C)=O>C1COCC1>[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([N:11]2[C@H:15]([C:16]([F:18])([F:19])[F:17])[C@@H:14]3[C@H:20]([OH:23])[CH2:21][CH2:22][N:13]3[C:12]2=[O:31])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]Participants
6
Procedure
To 66D (956 mg, 2.02 mmol) in THF (20 mL) was added a 1 M THF solution of TBAF (2.02 mL, 2.02 mmol). After stirring at rt for 1 h, additional TBAF was added (500 μL) and the reaction was stirred for 45 min. Saturated aqueous ammonium chloride and EtOAc were added and the layers were separated. The organic layer was washed with brine then dried (MgSO4), filtered and concentrated. The resulting residue was purified via preparative HPLC (YMC ODS C-18, 30×250 mm, eluting with 50-80% solvent B (A=90% H2O—10% MeOH and B=10% H2O—90% MeOH) over 15 min; Flow rate at 20 mL/min; UV detection at 220 nm) to provide the title compound (617 mg) as a white solid. MS: m/z 358 [M−H]−.
Workup
- stirringthe reaction was stirred for 45 min
- customthe layers were separated
- washThe organic layer was washed with brine
- dry with materialthen dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
- customThe resulting residue was purified via preparative HPLC (YMC ODS C-18, 30×250 mm
- washeluting with 50-80% solvent B (A=90% H2O—10% MeOH and B=10% H2O—90% MeOH) over 15 min
Sources & evidence
- ORD record
- ord-6e8c7f014a5f4928aaee8a8419eb1426
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07405234B2
Reaction notes
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