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

HRID 217520Notes

Reaction equation

HRID 217520 reaction equation
[CH3:1][O:2][C:3](=[O:40])[N:4]([CH2:18][C:19]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][C:20]=1[C:29]1[CH:34]=[C:33]([CH:35]([CH3:37])[CH3:36])[CH:32]=[CH:31][C:30]=1[O:38][CH3:39])[CH2:5][C:6]1[CH:11]=[C:10]([CH:12]=[CH2:13])[CH:9]=[C:8]([C:14]([F:17])([F:16])[F:15])[CH:7]=1>C1COCC1.CO.[Pd]>[CH3:1][O:2][C:3](=[O:40])[N:4]([CH2:5][C:6]1[CH:7]=[C:8]([C:14]([F:17])([F:16])[F:15])[CH:9]=[C:10]([CH2:12][CH3:13])[CH:11]=1)[CH2:18][C:19]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][C:20]=1[C:29]1[CH:34]=[C:33]([CH:35]([CH3:37])[CH3:36])[CH:32]=[CH:31][C:30]=1[O:38][CH3:39]

Participants

5

Reactant 1

HCID 11721070Methyl{[5'-isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}[3-(trifluoromethyl)-5-vinylbenzyl]carbamate

Product 1

HCID 11671357Methyl[3-ethyl-5-(trifluoromethyl)benzyl]{[5'-isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl{[5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}[3-(trifluoromethyl)-5-vinylbenzyl]carbamate (14 mg, 0.025 mmol) (Example 44) and Pd/C (5 mg) in THF (1 mL) and MeOH (500 μL) was placed under hydrogen. The reaction was stirred at room temperature under hydrogen for two hours. The reaction was then diluted with hexanes (25 mL), loaded on a silica gel column, and purified with 20% EtOAc/hexanes to afford methyl[3-ethyl-5-(trifluoromethyl)benzyl]{[5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate. Rf=0.31 (25% EtOAc/hexanes). LCMS=568.3 (M+1)+.1H NMR (C6D6, 500 MHz, 70° C.) δ 7.72 (broad singlet, 1H), 7.34 (d, J=7.5 Hz, 1H), 7.20 (s, 1H), 7.10 (s, 1H), 7.07 (d, J=8.0 Hz, 1H), 7.01 (dd, J=2.0 Hz, 8.5, 1H), 7.01 (broad singlet, 1H), 6.86 (d, J=2.5 Hz, 1H), 6.59 (d, J=8.5 Hz, 1H), 4.44 (broad singlet, 2H), 4.11 (broad singlet, 2H), 3.39 (s, 3H), 3.24 (s, 3H), 2.73 (m, 1H), 2.25 (q, J=7.5 Hz, 2H), 1.15 (d, J=7.0 Hz, 6H), 0.92 (t, J=7.5 Hz, 3H).

Workup

  1. custompurified with 20% EtOAc/hexanes

Sources & evidence

ORD record
ord-14e0049f0c094ccaa3763b6aafd77eea
Source dataset
uspto-grants-2012_06
Patent number
US08193365B2

Reaction notes

Loading…