Water → Methyl {[5'-isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}[3-nitro-5-(trifluoromethyl)benzyl]carbamate

HRID 217497Notes

Reaction equation

HRID 217497 reaction equation
[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([O:36][CH3:37])=[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][NH:21][CH2:22][C:23]2[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[C:25]([N+:33]([O-:35])=[O:34])[CH:24]=2)[CH:9]=1)([CH3:3])[CH3:2].Cl[C:39]([O:41][CH3:42])=[O:40].C(N(CC)C(C)C)(C)C.O>C(Cl)Cl>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([O:36][CH3:37])=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:18])([F:19])[F:17])=[CH:12][C:11]=2[CH2:20][N:21]([CH2:22][C:23]2[CH:28]=[C:27]([C:29]([F:30])([F:31])[F:32])[CH:26]=[C:25]([N+:33]([O-:35])=[O:34])[CH:24]=2)[C:39](=[O:40])[O:41][CH3:42])[CH:9]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 59343863{[5'-Isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}[3-nitro-5-(trifluoromethyl)benzyl]amine

Product 1

HCID 11534401Methyl {[5'-isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}[3-nitro-5-(trifluoromethyl)benzyl]carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {[5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}[3-nitro-5-(trifluoromethyl)benzyl]amine (428 mg, 0.81 mmol) and methyl chloroformate (126 μL, 1.39 mmol) in CH2Cl2 (10 mL) was added N,N-diisopropylethylamine (566 μL, 3.25 mmol). The reaction was stirred at room temperature for twenty minutes and then was poured into H2O (25 mL). The mixture was extracted with EtOAc (70 mL), and the organic extracts were washed with brine (25 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}[3-nitro-5-(trifluoromethyl)benzyl]carbamate. Rf=0.37 (25% EtOAc/hexanes). LCMS=585.3 (M+1)+. 1H NMR (C6D6, 500 MHz, 70° C.) δ 8.03 (s, 1H), 7.78 (s, 1H), 7.64 (s, 1H), 7.37 (s, 1H), 7.33 (d, J=8.0 Hz, 1H), 7.04-7.06 (m, 2H), 6.83 (s, 1H), 6.60 (d, J=8.4 Hz, 1H), 4.37 (bs, 2H), 3.93 (bs, 2H), 3.36 (s, 3H), 3.26 (s, 3H), 2.73 (m, 1H), 1.15 (d, J=6.8 Hz, 6H).

Workup

  1. extractionThe mixture was extracted with EtOAc (70 mL)
  2. washthe organic extracts were washed with brine (25 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-4fc5f1b7534e4a11bfdc40241a7c23ad
Source dataset
uspto-grants-2012_06
Patent number
US08193365B2

Reaction notes

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