Ethyl Acetate → HCID 178430158, compound

HRID 1864693Notes

Reaction equation

HRID 1864693 reaction equation
[Si]([O:8][C@@H:9]1[C@@:16]2([CH3:17])[N:12](/[C:13](=[N:18]/[C:19]3[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[C:21]([Cl:27])[C:20]=3[CH3:28])/[O:14][CH2:15]2)[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@@:16]2([CH3:17])[N:12](/[C:13](=[N:18]/[C:19]3[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[C:21]([Cl:27])[C:20]=3[CH3:28])/[O:14][CH2:15]2)[CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 178430160HCID 178430160, compound

Product 1

HCID 178430158HCID 178430158, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To compound 3E (8.0 mg, 0.0190 mmol) in THF (1 mL) was added a 1 M solution of TBAF in THF (0.190 mL, 0.190 mmol). After stirring at rt for 1.5 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-1 8, 21.2×100 mm, eluting with 40-100% solvent B (A=90% H2O-10% MeOH and B=10% H2O-90% MeOH) over 10 min; Flow rate at 20 mL/min; UV detection at 220 nm) to provide the title compound (4.0 mg) as a white solid. MS: m/z 306 [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-1 8, 21.2×100 mm
  7. washeluting with 40-100% solvent B (A=90% H2O-10% MeOH and B=10% H2O-90% MeOH) over 10 min

Sources & evidence

ORD record
ord-f94e8c351b3846b3ab02710e5e57e946
Source dataset
uspto-grants-2009_12
Patent number
US07625923B2

Reaction notes

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