Trifluoroacetic acid → HCID 22458860, compound

HRID 2184942Notes

Reaction equation

HRID 2184942 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([CH:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][N:21]4[CH2:26][CH2:25][CH2:24][CH:23]([CH3:27])[CH2:22]4)=[CH:14][CH:13]=3)O)=[C:8]([C:28]3[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=3)[S:7][C:6]=2[CH:35]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([CH2:10][C:12]3[CH:13]=[CH:14][C:15]([O:18][CH2:19][CH2:20][N:21]4[CH2:26][CH2:25][CH2:24][CH:23]([CH3:27])[CH2:22]4)=[CH:16][CH:17]=3)=[C:8]([C:28]3[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=3)[S:7][C:6]=2[CH:35]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 22458857HCID 22458857, compound

Product 1

HCID 22458860HCID 22458860, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of the product of Example 24 (0.466 g, 0.980 mmol) stirring in dichloromethane (24 mL) at 0° C. was added triethylsilane (0.94 mL, 5.8 mmol). After 10 minutes, trifluoroacetic acid (6.4 mL) was added at such a rate that the temperature was maintained below 5° C. The resulting solution was stirred at 0° C. for 2 hours, then quenched by pouring it into a saturated aqueous sodium bicarbonate solution (50 mL). Methanol was added as necessary to dissolve any residue. This mixture was then extracted with ethyl acetate (2×200 mL). The combined extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated. Purification by radial chromatography (4 mm, silica gel, 8:2 ethyl acetate/methanol) gave 0.304 g (68%) of the title compound as a white foam: 1H NMR (300 MHz, MeOD-d4) δ7.26-7.30 (m, 3H), 7.18 (d, 1H, J=2.2 Hz), 7.03 (d, 2H, J=8.6 Hz), 6.74-6.83 (m, 5H), 4.07-4.11 (m, 4H), 3.00-3.20 (m, 4H), 2.80-2.85 (m, 1H), 2.35-2.41 (m, 2H), 2.05-2.18 (m, 1H), 1.43-1.48 (m, 1H), 1.06 (t, 3H, J=6.2 Hz); IR (KBr) 3385, 2958, 1677, 1610, 1509, 1239, 837 cm−1; MS (FD) m/z 460 (m+).

Workup

  1. temperaturewas maintained below 5° C
  2. customquenched
  3. additionby pouring it into a saturated aqueous sodium bicarbonate solution (50 mL)
  4. additionMethanol was added as necessary
  5. dissolutionto dissolve any residue
  6. extractionThis mixture was then extracted with ethyl acetate (2×200 mL)
  7. dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by radial chromatography (4 mm, silica gel, 8:2 ethyl acetate/methanol)

Sources & evidence

ORD record
ord-246245a85a674464bf3721dbed5816bd
Source dataset
uspto-grants-2002_06
Patent number
US06399634B1

Reaction notes

Loading…