Ethyl Acetate → HCID 178430192, compound

HRID 1864707Notes

Reaction equation

HRID 1864707 reaction equation
[Si]([O:8][C@H:9]1[C@@H:16]2[N:12](/[C:13](=[N:21]/[C:22]3[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[C:24]([Cl:30])[C:23]=3[CH3:31])/[O:14][C@@H:15]2[C:17]([F:20])([F:19])[F:18])[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Cl-].[NH4+].CCOC(C)=O>C1COCC1>[OH:8][C@H:9]1[C@@H:16]2[N:12](/[C:13](=[N:21]/[C:22]3[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[C:24]([Cl:30])[C:23]=3[CH3:31])/[O:14][C@@H:15]2[C:17]([F:18])([F:20])[F:19])[CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 178430195HCID 178430195, compound

Product 1

HCID 178430192HCID 178430192, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 7G (140 mg, 0.296 mmol) in THF (2 mL) was added a 1 M THF solution of TBAF (0.400 1 nL, 0.400 mmol). After stirring at rt for 2 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 twice via preparative HPLC (YMC ODS C-1 8, 30×100 mm, eluting with 50-80% solvent B (A=90% H2O-10% MeOH and B=10% H2O-90% MeOH) over 15 min; Flow rate at 40 mL/min; UV detection at 220 nm) to provide the title compound (50.0 mg) as a white foam. MS: m/z 358 [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 twice via preparative HPLC (YMC ODS C-1 8, 30×100 mm
  7. 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-bef63dc1f229450dab340ce659a5c28c
Source dataset
uspto-grants-2009_12
Patent number
US07625923B2

Reaction notes

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