Potassium Carbonate → HCID 25101790, compound

HRID 1484138Notes

Reaction equation

HRID 1484138 reaction equation
FC(F)(F)C([NH:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11](/[CH:15]=[CH:16]/[C:17]([OH:24])([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])[CH:10]=1)=O.C([O-])([O-])=O.[K+].[K+]>>[NH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=1)/[CH:15]=[CH:16]/[C:17]([OH:24])([CH2:18][CH2:19][CH3:20])[CH2:21][CH2:22][CH3:23]

Participants

3

Reactant 2

HCID 11430Potassium CarbonateHCID 86632165HCID 86632165, compound

Product 1

HCID 25101790HCID 25101790, compound

Procedure

(E)-2,2,2-Trifluoro-N-(3-(3-(3-hydroxy-3-propylhex-1-enyl)phenyl)propyl)acetamide was deprotected according to the method used in Example 79 except that 3 equivalents of K2CO3 were used. Following the reaction, solids were removed by filtration and the filtrate was concentrated under reduced pressure. The residue was dissolved in MeOH, dried over MgSO4 and filtered through Celite. After concentration under reduced pressure, purification by flash chromatography (7:3 EtOAc:hexanes to 7:2:1 EtOAc:hexanes: 7 M NH3 in MeOH gradient) gave Example 83 as a single trans isomer. Yield (0.348 g, quant.): 1H NMR (400 MHz, DMSO-d3) δ 7.18-7.22 (m, 3H), 7.03-7.06 (m, 1H), 6.51 (d, J=16.0 Hz, 1H), 6.20 (d, J=16.4 Hz, 1H), 4.30 (br s, 1H), 2.66 (t, J=7.4 Hz, 2H), 2.64 (t, J=7.8 Hz, 2H), 1.75-1.82 (m, 2H), 1.53-1.59 (m, 4H), 1.33-1.44 (m, 4H), 0.92 (t, J=7.4 Hz, 6H).

Workup

  1. customthe reaction, solids
  2. customwere removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in MeOH
  5. dry with materialdried over MgSO4
  6. filtrationfiltered through Celite
  7. concentrationAfter concentration
  8. customunder reduced pressure, purification by flash chromatography (7:3 EtOAc:hexanes to 7:2:1 EtOAc:hexanes: 7 M NH3 in MeOH gradient)
  9. customgave Example 83 as a single trans isomer
  10. customYield (0.348 g, quant.)

Sources & evidence

ORD record
ord-682caccc2f5c498e8ad2fbe6d0e90406
Source dataset
uspto-grants-2016_08
Patent number
US09421210B2

Reaction notes

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