Trifluoroacetic acid → HCID 58909291, compound

HRID 1991522Notes

Reaction equation

HRID 1991522 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([C:10]2(O)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2].[N-:17]=[N+:18]=[N-:19].[Na+].FC(F)(F)C(O)=O.[OH-].[NH4+]>C(Cl)Cl.O.C(OCC)(=O)C.CCCCCCC>[CH:1]([C:4]1[CH:5]=[C:6]([C:10]2([N:17]=[N+:18]=[N-:19])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

9

Reactant 4

HCID 6422Trifluoroacetic acidHCID 14923Ammonium HydroxideHCID 33557Sodium AzideHCID 58909282HCID 58909282, compound

Product 1

HCID 58909291HCID 58909291, compoundYield 100%

Reagents, catalysts & solvents 4

HCID 962WaterSolvent3×HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolventHCID 8900HeptaneSolvent

Conditions

Temperature
-5 °C

Procedure

To 3.20 g (14.7 mmol) of compound 1 in 60 mL of CH2Cl2 under nitrogen is added 2.10 g (32.3 mmol) of sodium azide. The stirred suspension is cooled to −5° C. and a solution of trifluoroacetic acid (9.0 mL, 120 mmol) in 35 mL of dichloromethane is added dropwise over 1 h. The resulting suspension is stirred at 0° C. for an additional hour. To the cold, vigorously stirred mixture is added, dropwise, 10 mL of water, followed by dropwise addition of a mixture of 10 mL of water and 10 mL of concentrated ammonium hydroxide. After 30 min the mixture is poured into a separatory funnel containing 350 mL of a 1:1 mixture of heptane and ethyl acetate, and 100 mL of water. The organic phase is washed with an additional portion of water, followed successively by 1 N KH2PO4, water, and brine. It is then dried over anhydrous Na2SO4, filtered and concentrated to afford 3.6 g (14.7 mmol, 100%) of 2 as a pale yellow oil: 1H NMR (CDCl3) δ 7.3 (m, 2H), 7.25 (m, 1H), 7.16 (m, 1H), 2.92 (m, 1H), 2.01 (m, 2H), 1.83 (m, 2H), 1.73-1.64 (m, 5H), 1.3 (m, 1H), 1.26 (d, J=7 Hz, 6H).

Workup

  1. additionTo the cold, vigorously stirred mixture is added
  2. additionAfter 30 min the mixture is poured into a separatory funnel
  3. additioncontaining
  4. washThe organic phase is washed with an additional portion of water
  5. dry with materialIt is then dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3ac82be4c3204987b80626f16d83f3e6
Source dataset
uspto-grants-2010_01
Patent number
US07645780B2

Reaction notes

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