Methanol → HCID 69309788, compound

HRID 269992Notes

Reaction equation

HRID 269992 reaction equation
[C:1]([O:5][C:6](=[O:29])[N:7]([CH2:17][CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1)[CH2:8][CH2:9][NH:10]C(=O)C(F)(F)F)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].CO>O>[C:1]([O:5][C:6](=[O:29])[N:7]([CH2:8][CH2:9][NH2:10])[CH2:17][CH2:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 86610752HCID 86610752, compound

Product 1

HCID 69309788HCID 69309788, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Add [3-(4-Nitro-phenyl)-propyl]-[2-(2,2,2-trifluoro-acetylamino)-ethyl]carbamic acid tert-butyl ester (16 g, 33 mmol), potassium carbonate (23 g, 170 mmol), methanol (100 mL) and water (45 mL) to a 500 mL flask. Heat to 50° C. for 1 hr. Cool the reaction and filter off any solids. Add dichloromethane and water, stir and separated the layers. Extract the aqueous layer with dichloromethane. Combine the organic layers, wash with brine, dry over MgSO4 and concentrate under reduced pressure to obtain the title compound as an oily residue. The title compound was used without purification. 1H NMR (CDCl3, 500.0 MHz): δ 8.13 (d, 2H, J=9 Hz), 7.32 (d, 2H, J=8.5 Hz), 3.24 (br m, 4H), 2.82 (br m, 2H), 2.69 (t, 2H, J=7.5 Hz), 1.87 (p, J=7.5 Hz), 1.48 (br s, 2H), 1.43 (s, 9H).

Workup

  1. temperatureCool
  2. customthe reaction
  3. filtrationfilter off any solids
  4. customseparated the layers
  5. extractionExtract the aqueous layer with dichloromethane
  6. washwash with brine
  7. dry with materialdry over MgSO4
  8. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-faee04a07346438fb59ae88d9194398d
Source dataset
uspto-grants-2008_11
Patent number
US07449477B2

Reaction notes

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