(Diethylamino)sulfur trifluoride → HCID 59017206, compound

HRID 969269Notes

Reaction equation

HRID 969269 reaction equation
O[C@H:2]1[CH2:11][N:10]2[C@H:4]([CH2:5][O:6][C:7]3[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=3[C:9]2=[O:12])[CH2:3]1.C(N(S(F)(F)[F:23])CC)C.C([O-])(O)=O.[Na+]>C(OCC)(=O)C>[F:23][C@@H:2]1[CH2:11][N:10]2[C@H:4]([CH2:5][O:6][C:7]3[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=3[C:9]2=[O:12])[CH2:3]1

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 59017210HCID 59017210, compound

Product 1

HCID 59017206HCID 59017206, compoundYield 29.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of the material prepared in Example 25 (200 mg; 0.91 mmol) in dry ethyl acetate (10 ml) was cooled to −50° C. and (diethylamino)sulphur trifluoride (191 mg; 1.19 mmol) was added dropwise. The resultant solution was stirred at −50° C. for 1 h and then allowed to slowly warm to room temperature over a period of 3 h. The mixture was then poured onto a saturated aqueous NaHCO3 solution (50 ml) and further ethyl acetate (50 ml) added. After thorough mixing the organic layer was separated, washed sequentially with water (50 ml) and brine (50 ml), and dried (Na2SO4). The solvent was evaporated under reduced pressure and the residue was purified by flash chromatography to give the title compound as a pale yellow crystalline solid (60 mg). 1H NMR (CDCl3) δ 2.13 to 2.48 (m, 2H), 3.79 (qd, 1H), 4.09 (t, 1H), 4.25 to 4.35 (m, 2H), 4.43-4.49 (m, 1H), 5.333 (d, 1H), 7.04 (d, 1H) 7.15 (t, 1H), 7.41 (dd, 1H), 7.88 (dd, 1H); EIMS: m/z=222.2 [M+H]+

Workup

  1. additionadded
  2. additionAfter thorough mixing the organic layer
  3. customwas separated
  4. washwashed sequentially with water (50 ml) and brine (50 ml)
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-b2c33a1e46cd407cae08dfa239277771
Source dataset
uspto-grants-2007_12
Patent number
US07307073B2

Reaction notes

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