Trifluoroacetic acid → HCID 86614410, compound

HRID 227176Notes

Reaction equation

HRID 227176 reaction equation
C(O)(C(F)(F)F)=O.[CH2:8]([O:52][CH:53]1[C@H:57]2[C@H:58](OC3CCCCO3)[N:59](C(OC(C)(C)C)=O)[C:60]3[CH:67]=[C:66]([O:68][CH3:69])[CH:65]=[CH:64][C:61]=3[C:62](=[O:63])[N:56]2[CH2:55][CH2:54]1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][CH:21]1[C@H:25]2[C@H:26](OC3CCCCO3)[N:27](C(OC(C)(C)C)=O)[C:28]3[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[CH:32][C:29]=3[C:30](=[O:31])[N:24]2[CH2:23][CH2:22]1.C([O-])(O)=O.[Na+]>CO.C(Cl)(Cl)Cl>[CH2:19]([O:20][CH:21]1[C@@H:25]2[CH:26]=[N:27][C:28]3[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[CH:32][C:29]=3[C:30](=[O:31])[N:24]2[CH2:23][CH2:22]1)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][O:52][CH:53]1[C@@H:57]2[CH:58]=[N:59][C:60]3[CH:67]=[C:66]([O:68][CH3:69])[CH:65]=[CH:64][C:61]=3[C:62](=[O:63])[N:56]2[CH2:55][CH2:54]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86614411HCID 86614411, compound

Product 1

HCID 86614410HCID 86614410, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

95% TFA (3 mL) was added drop-wise to dimer compound 8j (208 mg, 0.19 mmol) at 0° C. This was then stirred for 1 hr and the mixture was poured into saturated NaHCO3 (30 mL) solution to naturalize the reaction mixture. The mixture was extracted with chloroform (3×20 mL). The organic layer was then washed water (20 mL), brine (20 mL) then dried (MgSO4) and filtrated. The excess solvent was removed under reduced pressure to give the crude product, which was subjected to flash column chromatography (SiO2, 2% methanol-chloroform). Removal of excess eluent under reduced pressure without heating afforded the final product 9j (107 mg, 0.16 mmol, 85%) as a solid: [α]20D=+506° (c=0.15, CHCl3); 1H NMR (CDCl3, 400 MHz): δ 1.26-1.52 (m, 16H, 14-H, 14′-H, 15-H, 15′-H, 16-H, 16′-H, 17-H, 17′-H), 1.83-1.92 (m, 4H, 13-H, 13′-H), 2.01-2.12 (m, 4H, 2-H, 2′-H), 2.28-2.37 (m, 4H, 1-H, 1′-H), 3.55-3.64 (m, 2H, 3-H, 3′-H), 3.70-3.77 (m, 2H, 11a-H, 11a′-H), 3.78-3.87 (m, 2H, 3-H, 3′-H), 3.92 (s, 6H, 7-OMe, 7′-OMe), 4.03-4.19 (m, 4H, 12-H, 12′-H), 6.81 (s, 2H, 9-H, 9′-H), 7.52 (s, 2H, 6-H, 6′-H), 7.67 (d, 2H, J=4, 11-H, 11′-H); 13C NMR (CDCl3, 400 MHz): δ 24.1, 25.9, 29.0, 29.3, 29.54, 29.57, 29.6, 46.6, 53.7, 56.0, 69.1, 109.6, 112.5, 120.2, 140.5, 147.1, 151.6, 162.2, 164.6,; IR (neat): 3338, 2926, 1600, 1507, 1448, 1261, 1217, 1024 cm−1; MS (FAB) m/z (relative intensity) 723 ([M+2×MeOH]+., 14), 691 ([M+MeOH]+., 20), 659 (M+., 100).

Workup

  1. extractionThe mixture was extracted with chloroform (3×20 mL)
  2. dry with materialwashed water (20 mL), brine (20 mL) then dried (MgSO4)
  3. filtrationfiltrated
  4. customThe excess solvent was removed under reduced pressure
  5. customto give the crude product, which
  6. customRemoval of excess eluent under reduced pressure
  7. temperaturewithout heating

Sources & evidence

ORD record
ord-348de8b16e604e6d8eb66ce51f6fa489
Source dataset
uspto-grants-2009_07
Patent number
US07557099B2

Reaction notes

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