p-(Trifluoromethoxy)phenyl isocyanate → HCID 86594050, compound

HRID 898869Notes

Reaction equation

HRID 898869 reaction equation
[C:1]([O:5][C:6](=[O:24])[C:7]([S:10][C:11]1[CH:20]=[CH:19][C:18]2[CH2:17][CH:16]([NH:21][CH2:22][CH3:23])[CH2:15][CH2:14][C:13]=2[CH:12]=1)([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[F:25][C:26]([F:38])([F:37])[O:27][C:28]1[CH:33]=[CH:32][C:31]([N:34]=[C:35]=[O:36])=[CH:30][CH:29]=1>C(Cl)Cl>[C:1]([O:5][C:6](=[O:24])[C:7]([S:10][C:11]1[CH:20]=[CH:19][C:18]2[CH2:17][CH:16]([N:21]([CH2:22][CH3:23])[C:35]([NH:34][C:31]3[CH:32]=[CH:33][C:28]([O:27][C:26]([F:25])([F:37])[F:38])=[CH:29][CH:30]=3)=[O:36])[CH2:15][CH2:14][C:13]=2[CH:12]=1)([CH3:9])[CH3:8])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 92298p-(Trifluoromethoxy)phenyl isocyanateHCID 688125622-(6-Ethylamino-5,6,7,8-tetrahydronaphthalen-2-ylsulfanyl)-2-methylpropionic acid tert-butyl ester

Product 1

HCID 86594050HCID 86594050, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-(6-ethylamino-5,6,7,8-tetrahydronaphthalen-2-ylsulfanyl)-2-methylpropionic acid tert-butyl ester and borane complex (1.9 g; 5.2 mmol) dissolved in CH2Cl2 (15 mL) is added 4-trifluoromethoxyphenyl isocyanate (1.6 g; 7.8 mmol) and the reaction was stirred at RT for 18 h. The solvent was removed under reduced pressure and the crude residue was purified by flash chromatography (SiO2) eluting with a hexanes-EtOAc gradient to provide 1.66 g (58%) of 2-{6-[1-ethyl-3-(4-trifluoromethoxyphenyl)ureido]-5,6,7,8-tetrahydronaphthalen-2-ylsulfanyl}-2-methylpropionic acid tert butyl ester as a white foam.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude residue was purified by flash chromatography (SiO2)
  3. washeluting with a hexanes-EtOAc gradient

Sources & evidence

ORD record
ord-16437502459041d19a34cbe507dbe279
Source dataset
uspto-grants-2008_04
Patent number
US07351857B2

Reaction notes

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