Potassium Carbonate → [3-Phenyl-2,2-bis-(3-trifluoromethoxy-phenyl)-propyl]-carbamic acid 4-nitro-phenyl ester

HRID 1952407Notes

Reaction equation

HRID 1952407 reaction equation
[C:1]1([CH2:7][C:8]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:29]([F:32])([F:31])[F:30])[CH:23]=2)([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]([F:21])([F:20])[F:19])[CH:12]=2)[CH2:9][NH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].[C:39](Cl)(=[O:50])[O:40][C:41]1[CH:46]=[CH:45][C:44]([N+:47]([O-:49])=[O:48])=[CH:43][CH:42]=1>C(Cl)Cl>[N+:47]([C:44]1[CH:43]=[CH:42][C:41]([O:40][C:39](=[O:50])[NH:10][CH2:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]([F:21])([F:20])[F:19])[CH:12]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:29]([F:30])([F:31])[F:32])[CH:23]=2)[CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:46][CH:45]=1)([O-:49])=[O:48]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 821294-Nitrophenyl chloroformateHCID 591926393-Phenyl-2,2-bis(3-(trifluoromethoxy)phenyl)propan-1-amine

Product 1

HCID 59192652[3-Phenyl-2,2-bis-(3-trifluoromethoxy-phenyl)-propyl]-carbamic acid 4-nitro-phenyl esterYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-phenyl-2,2-bis(3-(trifluoromethoxy)phenyl)propan-1-amine (1.37 g, 3.00 mmol), prepared as described in Example 10 (Procedure 13, 14, 15, and 16), in CH2Cl2 (35 mL) was added K2CO3 (2.1 g, 15 mmol) followed by 4-nitrophenyl carbonochloridate (806 mg, 4.0 mmol) and the reaction mixture was stirred at rt for 5 h. The reaction mixture was diluted with CH2Cl2 (25 mL) and washed with 1N Na2CO3 (6×50 mL), then dried over Na2SO4, filtered and concentrated under reduced pressure to yield a residue. The residue was purified on a silica gel ISCO cartridge with elution at 0 to 40% EtOAc/hexane to yield [3-phenyl-2,2-bis-(3-trifluoromethoxy-phenyl)-propyl]-carbamic acid 4-nitro-phenyl ester (1.50 g, 81% yield) as a clear, colorless oil. LCMS: RT=2.30 min [M+H] 620.94 (2 min Phenomenex Luna C18 column, 4.6×30 mm eluting with 10-90% MeOH/H2O over 2 minutes containing 0.1% TFA; 5 mL/min, monitoring at 220 nm); NMR: 400 MHz 1H (CDCl3) ppm 3.42 (s, 2 H), 3.92 (d, J=6.15 Hz, 2 H), 4.72 (t, J=5.71 Hz, 1 H), 6.60 (d, J=7.03 Hz, 2 H), 7.05-7.26 (m, 9 H), 7.37 (t, J=8.13 Hz, 2 H), 8.23 (d, J=9.23 Hz, 2 H).

Workup

  1. washwashed with 1N Na2CO3 (6×50 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto yield a residue
  6. customThe residue was purified on a silica gel ISCO cartridge with elution at 0 to 40% EtOAc/hexane

Sources & evidence

ORD record
ord-a5464a4257174e3aa74323469ba33e19
Source dataset
uspto-grants-2013_03
Patent number
US08404896B2

Reaction notes

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