Trifluoroacetic acid → 2-{6-[1-Ethyl-3-(4-trifluoromethoxyphenyl)ureido]-5,6,7,8-tetrahydronaphthalen-2-ylsulfanyl}-2-methylpropionic acid

HRID 2104265Notes

Reaction equation

HRID 2104265 reaction equation
C([O:5][C:6](=[O:40])[C:7]([S:10][C:11]1[C:20](OC)=[CH:19][C:18]2[CH2:17][CH:16]([N:23]([CH2:38][CH3:39])[C:24]([NH:26][C:27]3[CH:32]=[CH:31][C:30]([O:33][C:34]([F:37])([F:36])[F:35])=[CH:29][CH:28]=3)=[O:25])[CH2:15][CH2:14][C:13]=2[CH:12]=1)([CH3:9])[CH3:8])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:38]([N:23]([CH:16]1[CH2:15][CH2:14][C:13]2[CH:12]=[C:11]([S:10][C:7]([CH3:8])([CH3:9])[C:6]([OH:40])=[O:5])[CH:20]=[CH:19][C:18]=2[CH2:17]1)[C:24]([NH:26][C:27]1[CH:28]=[CH:29][C:30]([O:33][C:34]([F:37])([F:35])[F:36])=[CH:31][CH:32]=1)=[O:25])[CH3:39]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86601316HCID 86601316, compound

Product 1

HCID 102552732-{6-[1-Ethyl-3-(4-trifluoromethoxyphenyl)ureido]-5,6,7,8-tetrahydronaphthalen-2-ylsulfanyl}-2-methylpropionic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2-{6-[1-ethyl-3-(4-trifluoromethoxyphenyl)ureido]-3-methoxy-5,6,7,8-tetrahydronaphthalen-2-ylsulfanyl}-2-methylpropionic acid tert butyl ester (0.02 g; 0.03 mmol) dissolved in CH2Cl2 (1.5 mL) was added TFA (1.5 mL) and the reaction mixture was stirred at room temperature for 1.5 h. The solvent was removed under reduced pressure and the residue was purified by reverse-phase semi-prep HPLC eluting with a MeCN—H2O gradient to yield 2-{6-[1ethyl-3-(4-trifluoromethoxyphenyl)ureido]-5,6,7,8-tetrahydronaphthalen-2-ylsulfanyl}-2-methylpropionic acid as a white solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by reverse-phase semi-prep HPLC
  3. washeluting with a MeCN—H2O gradient

Sources & evidence

ORD record
ord-49bd0cea88484ce482fece0a6ccef0ea
Source dataset
uspto-grants-2009_08
Patent number
US07576238B2

Reaction notes

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