Trifluoroacetic acid → HCID 66916290, compound

HRID 227183Notes

Reaction equation

HRID 227183 reaction equation
C(O)(C(F)(F)F)=O.[CH2:8]([O:48][CH:49]1[C@H:53]2[C@H:54](OC3CCCCO3)[N:55](C(OC(C)(C)C)=O)[C:56]3[CH:63]=[CH:62][C:61]([O:64][CH3:65])=[CH:60][C:57]=3[C:58](=[O:59])[N:52]2[CH2:51][CH2:50]1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][CH:17]1[C@H:21]2[C@H:22](OC3CCCCO3)[N:23](C(OC(C)(C)C)=O)[C:24]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][C:25]=3[C:26](=[O:27])[N:20]2[CH2:19][CH2:18]1.C([O-])(O)=O.[Na+]>CO.C(Cl)(Cl)Cl>[CH2:8]([O:48][CH:49]1[C@@H:53]2[CH:54]=[N:55][C:56]3[CH:63]=[CH:62][C:61]([O:64][CH3:65])=[CH:60][C:57]=3[C:58](=[O:59])[N:52]2[CH2:51][CH2:50]1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][CH:17]1[C@@H:21]2[CH:22]=[N:23][C:24]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][C:25]=3[C:26](=[O:27])[N:20]2[CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86614421HCID 86614421, compound

Product 1

HCID 66916290HCID 66916290, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

95% TFA (3 mL) was added drop-wise to dimer compound 15f (190 mg, 0.18 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 16f (105 mg, 0.17 mmol, 96%) as a solid: [α]20D=+1330° (c=0.13, CHCl3); 1H NMR (CDCl3, 400 MHz): δ 1.32-1.58 (m, 8H, 14-H, 14′-H, 15-H, 15′-H), 1.78-1.92 (m, 4H, 13-H, 13′-H), 1.93-2.10 (m, 4H, 2-H, 2′-H), 2.26-2.38 (m, 4H, 1-H, 1′-H), 3.55-3.64 (m, 2H, 3-H, 3′-H), 3.70-3.76 (m, 2H, 11a-H, 11a′-H), 3.77-3.89 (m, 2H, 3-H, 3′-H), 3.93 (s, 6H, 7-OMe, 7′-OMe), 3.98-4.15 (m, 4H, 12-H, 12′-H), 6.79 (s, 2H, 9-H, 9′-H), 7.51 (s, 2H, 6-H, 6′-H), 7.65 (d, 2H, J=4.4, 11-H, 11′-H); 13C NMR (CDCl3, 400 MHz): δ 24.1, 25.8, 28.8, 29.2; 29.6; 46.6; 53.7, 56.1, 69.0, 110.4, 111.6, 120.0, 140.6, 147.8, 150.9, 162.2, 164.67; IR (neat): 3326, 2934, 1599, 1505, 1455, 1431, 1382, 1261, 1216, 1092, 1019 cm−1; MS (FAB) m/z (relative intensity) 667 ([M+2×MeOH]+., 3), 635 ([M+MeOH]+., 8), 603 (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-534afd05abf34f65982ac12e4c1ac9df
Source dataset
uspto-grants-2009_07
Patent number
US07557099B2

Reaction notes

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