Trifluoroacetic anhydride → HCID 68864572, compound

HRID 1726000Notes

Reaction equation

HRID 1726000 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[C:13]([C:25]([O:27][CH3:28])=[O:26])=[C:14]([CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=O)[CH:15]=[CH:16][CH:17]=1)(=[O:10])=[O:9].FC(F)(F)C(OC(=O)C(F)(F)F)=O.[O-]S(C(F)(F)F)(=O)=O.[Ga+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>ClC(Cl)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[C:13]([C:25]([O:27][CH3:28])=[O:26])=[C:14]2[CH2:18][CH2:19][CH2:20][CH2:21][C:22](=[O:24])[C:15]2=[CH:16][CH:17]=1)(=[O:9])=[O:10]

Participants

5

Reactant 3

HCID 9845Trifluoroacetic anhydrideHCID 2733940GALLIUM(III) TRIFLUOROMETHANESULFONATEHCID 68866177HCID 68866177, compound

Product 1

HCID 68864572HCID 68864572, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of Example 510E (3.74 g, 9.13 mmol) in dichloroethane (183 mL) was treated with trifluoroacetic anhydride (2.58 mL, 18.3 mmol) and gallium (III) triflate (0.944 g, 1.83 mmol), stirred at 90° C. for 1.5 hours, and cooled to room temperature. The reaction was quenched with saturated aqueous sodium bicarbonate (200 mL), and the aqueous layer was extracted with CH2Cl2 (4×50 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash chromatography (7:3 hexanes/ethyl acetate) to provide the desired product (2.73 g, 76%). MS (ESI(+)) m/e 392 (M+H)+, 409 (M+NH4)+, 414 (M+Na)+; MS (ESI(−)) m/e 390 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 10.46 (br s, 1H), 7.74 (m, 2H), 7.52 (d, 1H), 7.43 (dd, 1H), 7.35 (td, 1H), 7.25 (d, 1H), 3.70 (s, 3H), 2.67 (t, 2H), 2.61 (m, 2H), 1.72 (m, 2H), 1.60 (m, 2H).

Workup

  1. temperaturecooled to room temperature
  2. customThe reaction was quenched with saturated aqueous sodium bicarbonate (200 mL)
  3. extractionthe aqueous layer was extracted with CH2Cl2 (4×50 mL)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by flash chromatography (7:3 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-7b8b18f9400b4abe850cd9c8c69f045d
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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