Ethyl Acetate → HCID 59128678, compound

HRID 1991113Notes

Reaction equation

HRID 1991113 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]3[C:14]([C:15]4[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=4)=[CH:13][N:12](COCC[Si](C)(C)C)[C:9]3=[N:10][CH:11]=2)[CH2:3][CH2:2]1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].CCOC(C)=O.C([O-])(O)=O.[Na+]>C1COCC1>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]3[C:14]([C:15]4[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=4)=[CH:13][NH:12][C:9]3=[N:10][CH:11]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 59128677HCID 59128677, compound

Product 1

HCID 59128678HCID 59128678, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 28s (40 mg, 0.10 mmol) and 1.0 M TBAF in THF (3 mL) was heated at reflux for 7 h. The reaction mixture was then cooled, poured onto a mixture of AcOEt and saturated aqueous NaHCO3. The layers were separated, the aqueous phase extracted with more AcOEt (2×) then the combined organic extracts dried (MgSO4) and concentrated. The residue was purified by PTLC using 5% MeOH in CH2Cl2 as eluent) to give 29s as a white solid (25.0 mg, 62%); 1H NMR (400 MHz, CDCl3) δ 0.40 (q, J=4.7 Hz, 2H), 0.69 (m, 2H), 1.33 (m, 1H), 3.91 (d, J=7.0 Hz, 2H), 4.00 (s, 3H), 7.36 (d, J=2.5 Hz, 1H), 7.56 (d, J=2.5 Hz, 1H), 7.60 (s, 1H), 7.75 (s, 1H), 8.15 (d, J=2.6 Hz, 1H), 9.14 (bs, NH).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 7 h
  3. temperatureThe reaction mixture was then cooled
  4. customThe layers were separated
  5. extractionthe aqueous phase extracted with more AcOEt (2×)
  6. dry with materialthe combined organic extracts dried (MgSO4)
  7. concentrationconcentrated
  8. customThe residue was purified by PTLC

Sources & evidence

ORD record
ord-c507adfc0566488386ec339dca62fb51
Source dataset
uspto-grants-2010_01
Patent number
US07645769B2

Reaction notes

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