Ethyl Acetate → HCID 16731844, compound

HRID 751157Notes

Reaction equation

HRID 751157 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

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 16731679HCID 16731679, compound

Product 1

HCID 16731844HCID 16731844, compoundYield 6.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 75F (8.20 mg, 0.173 mmol) in THF (2 mL) was added a 1 M THF solution of TBAF (0.120 mL, 0.120 mmol). After stirring at rt for 1 h, 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 50-90% 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 (4.10 mg) as a white solid. MS: m/z 360 [M+H]+.

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with brine
  3. dry with materialthen dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was purified via preparative HPLC (YMC ODS C-18, 30×250 mm
  7. washeluting with 50-90% solvent B (A=90% H2O—10% MeOH and B=10% H2O—90% MeOH) over 15 min

Sources & evidence

ORD record
ord-662a2a683ea44e78978c44103c04d6b8
Source dataset
uspto-grants-2008_07
Patent number
US07405234B2

Reaction notes

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