Water → Methyl {[5'-isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate

HRID 217493Notes

Reaction equation

HRID 217493 reaction equation
[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([O:22][CH3:23])=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:11]=2[CH2:20][NH2:21])[CH:9]=1)([CH3:3])[CH3:2].Cl[C:25]([O:27][CH3:28])=[O:26].C(N(CC)C(C)C)(C)C.O>C(Cl)Cl>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([O:22][CH3:23])=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:17])([F:18])[F:19])=[CH:12][C:11]=2[CH2:20][NH:21][C:25](=[O:26])[O:27][CH3:28])[CH:9]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 591351271-[5'-Isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methanamine

Product 1

HCID 59343870Methyl {[5'-isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methanamine (166 mg, 0.51 mmol) and methyl chloroformate (107 μL, 1.39 mmol) in CH2Cl2 (5 mL) was added N,N-diisopropylethylamine (485 μL, 2.79 mmol). The reaction was stirred at room temperature for twenty minutes and then was poured into H2O (50 mL). The mixture was extracted with EtOAc (100 mL), and the organic layer was washed with brine (50 mL), dried over Na2SO4, filtered, and concentrated. Purification by flash chromatography with 2% to 20% EtOAc/hexanes afforded methyl {[5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate. Rf=0.29 (15% EtOAc/hexanes). LCMS=382.3 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 7.68 (s, 1H), 7.57 (d, J=8.0 Hz, 1H), 7.31 (d, J=8.0 Hz, 1H), 7.25 (dd, J=8.5, 2.5 Hz, 1H), 6.97 (d, J=2.5 Hz, 1H), 6.91 (d, J=8.5 Hz, 1H), 4.17 (m, 2H), 3.75 (s, 3H), 3.65 (s, 3H), 2.89 (m, 1H), 1.25 (d, J=7.0 Hz, 6H).

Workup

  1. extractionThe mixture was extracted with EtOAc (100 mL)
  2. washthe organic layer was washed with brine (50 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography with 2% to 20% EtOAc/hexanes

Sources & evidence

ORD record
ord-1b110d5e1e754a5cbf36fc488f5a1906
Source dataset
uspto-grants-2012_06
Patent number
US08193365B2

Reaction notes

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