Water → HCID 10632831, compound

HRID 2111458Notes

Reaction equation

HRID 2111458 reaction equation
[C:1]([S:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2OCC(C)(C)C[O:15]2)=[CH:10][CH:9]=1)(=[O:3])[CH3:2].C(O)(C(F)(F)F)=O.O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]([S:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([CH:14]=[O:15])=[CH:12][CH:13]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 10518900HCID 10518900, compound

Product 1

HCID 10632831HCID 10632831, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 14 (525 mg, 1.70 mmol) was dissolved in CH2Cl2 (10 mL) and TFA (2.0 mL) was added together with a drop of water. The solution was stirred for 15 h at rt. Then aq NaHCO3 (5%, 35 mL) was added and the phases were separated. The organic phase was washed twice with aq NaHCO3 (5%), once with brine and dried (Na2SO4). The solvents were removed under reduced pressure and the oily residue was purified by column chromatography (silica, ether/hexanes, 1:2), affording a yellow oil (279 mg, 74%). IR (neat): {tilde over (v)} 3037, 2928, 2849, 2731, 1693, 1605; 1H NMR δ 1.88-1.99 (m, 2H), 2.35 (s, 3H), 2.78 (t, 3J=7.3Hz, 2H), 2.89 (t, 3J=7.3Hz, 2H), 7.35, 7.81 (AA′BB′, 2×2H), 9.98 (s, 1H); 13C NMR (APT) δ 28.1 (+), 30.4 (+), 34.7 (+), 128.8 (−), 129.7 (−), 134.4 (+), 148.3 (+), 191.6 (−), 195.2 (+); GC-MS (EI) obsd 222, 180, 146, 133, 117, 105, 91, 43.

Workup

  1. customthe phases were separated
  2. washThe organic phase was washed twice with aq NaHCO3 (5%), once with brine
  3. dry with materialdried (Na2SO4)
  4. customThe solvents were removed under reduced pressure
  5. customthe oily residue was purified by column chromatography (silica, ether/hexanes, 1:2)

Sources & evidence

ORD record
ord-f5cb77a6221d416bb4f1d30e87f3ec20
Source dataset
uspto-grants-2009_04
Patent number
US07518905B2

Reaction notes

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