Ethyl Acetate → HCID 91060211, compound

HRID 2307756Notes

Reaction equation

HRID 2307756 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C@H:11]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:12][O:13][C:14]2[CH:15]=[N:16][CH:17]=[C:18]([C:20]#[C:21][Si](C)(C)C)[CH:19]=2)=[CH:2]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>C1COCC1>[C:20]([C:18]1[CH:19]=[C:14]([O:13][CH2:12][C@@H:11]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:31])([CH3:30])[CH3:32])[CH2:10][C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][CH:2]=2)[CH:15]=[N:16][CH:17]=1)#[CH:21]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 91211023HCID 91211023, compound

Product 1

HCID 91060211HCID 91060211, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 14A (400 mg, 0.86 mmol) in THF (6 mL) at room temperature was treated with tetrabutylammonium fluoride (1.0 M solution in THF, 1.12 mL, 1.12 mmol), stirred for 1 hour, treated with ethyl acetate (50 mL), washed with brine, dried (MgSO4), filtered, and concentrated. The residual oil was purified by flash column chromatography on silica gel with 40% ethyl acetate/hexanes to provide the desired product (290 mg, 86%). MS (APCI) m/e 392 (M+H)+.

Workup

  1. washwashed with brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residual oil was purified by flash column chromatography on silica gel with 40% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-f766e643a9524b15bb9a19f962ce7ed7
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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