Sodium Bicarbonate → HCID 86720225, compound

HRID 625158Notes

Reaction equation

HRID 625158 reaction equation
[Br:1][C:2]1[C:3]([CH3:33])=[C:4]([CH2:17][CH:18]([N+:30]([O-:32])=[O:31])[C:19]([CH3:29])([CH3:28])[CH2:20][C:21](=[O:27])[CH:22]([O:25][CH3:26])[O:23][CH3:24])[N:5](S(C2C=CC(C)=CC=2)(=O)=O)[CH:6]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C([O-])(O)=O.[Na+]>C(OCC)(=O)C>[Br:1][C:2]1[C:3]([CH3:33])=[C:4]([CH2:17][CH:18]([N+:30]([O-:32])=[O:31])[C:19]([CH3:29])([CH3:28])[CH2:20][C:21](=[O:27])[CH:22]([O:25][CH3:26])[O:23][CH3:24])[NH:5][CH:6]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 86720226HCID 86720226, compound

Product 1

HCID 86720225HCID 86720225, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Following a general procedure,50 a sample of 6-Ts (9.12 g, 16.7 mmol) was treated with TBAF (34 mL, 1.0 M in THF, 34 mmol), and the reaction mixture was stirred for 1 h at reflux. A saturated solution of aqueous NaHCO3 (100 mL) was added followed by ethyl acetate (50 mL). The mixture was extracted with ethyl acetate. The organic layer was dried (Na2SO4), concentrated to a brown oil, dried under high vacuum for 2 h, and chromatographed (silica, CH2Cl2) to give a light brown oil (4.00 g, 61%): 1H NMR δ 1.13 (s, 3H), 1.22 (s, 3H), 1.95 (s, 3H), 2.60, 2.70 (AB, 2J=18.8 Hz, 2H), 2.99 (ABX, 2JAB=15.4 Hz, 3JBX=2.5 Hz, 1H), 3.24 (ABX, 2JAB=15.4 Hz, 3JAX=11.8 Hz, 1H), 3.41 (s, 3H), 3.42 (s, 3H), 4.38 (s, 1H), 5.12 (ABX, 3JAX=11.8 Hz, 3JBX=2.5 Hz, 1H), 6.59 (s, 1H), 8.29 (brs, 1H); 13C NMR δ 9.8, 24.4, 24.4, 25.6, 36.6, 45.4, 55.39, 55.40, 94.1, 99.0, 104.7, 116.1, 116.7, 122.5, 204.2; ESI-MS obsd 391.0864, calcd 391.0863 [(M+H)+, M=C15H23BrN2O5].

Workup

  1. temperatureat reflux
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated to a brown oil
  5. customdried under high vacuum for 2 h
  6. customchromatographed (silica, CH2Cl2)

Sources & evidence

ORD record
ord-9aa9a9a588d549219ea597c4e7eb00c0
Source dataset
uspto-grants-2016_04
Patent number
US09303165B2

Reaction notes

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