Ethyl Acetate → HCID 16731847, compound

HRID 501629Notes

Reaction equation

HRID 501629 reaction equation
[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([N:11]2[C@H:15]([CH:16]([CH3:18])[CH3:17])[C@@H:14]3[C@H:19]([O:22][Si](C(C)(C)C)(C)C)[CH2:20][CH2:21][N:13]3[C:12]2=[O:30])[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]([CH:16]([CH3:18])[CH3:17])[C@@H:14]3[C@H:19]([OH:22])[CH2:20][CH2:21][N:13]3[C:12]2=[O:30])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 59754270HCID 59754270, compound

Product 1

HCID 16731847HCID 16731847, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 71C (2.00 g, 4.47 mmol) in THF (45 mL) was added a 1 M THF solution of TBAF (4.47 mL, 4.47 mmol). After stirring at rt 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 flash chromatography eluting with 75-100% EtOAc/hexane to provide the title compound (1.36 g) which contained a minor impurity (6.76%). To obtain an analytically pure sample, a portion of the product (ca. 250 mg) was purified via preparative HPLC (YMC ODS C-18, 30×100 mm, eluting with 25% solvent B (solvent B=10% H2O-90% CH3CN-0.1% TFA) for 25 min; Flow rate at 40 mL/min; UV detection at 220 nm) to provide, after recrystallization from MeOH/water, the title compound (106 mg) as white needles. MS: m/z 665 [2M−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 flash chromatography
  7. washeluting with 75-100% EtOAc/hexane

Sources & evidence

ORD record
ord-29fc6da0add348cda6b5faf61b171a19
Source dataset
uspto-grants-2010_08
Patent number
US07772267B2

Reaction notes

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