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

HRID 898870Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 898870
C([O:5][C:6](=[O:38])[C:7]([S:10][C:11]1[CH:20]=[CH:19][C:18]2[CH2:17][CH:16]([N:21]([CH2:36][CH3:37])[C:22]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][C:32]([F:35])([F:34])[F:33])=[CH:27][CH:26]=3)=[O:23])[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>[CH2:36]([N:21]([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:38])=[O:5])[CH:20]=[CH:19][C:18]=2[CH2:17]1)[C:22]([NH:24][C:25]1[CH:26]=[CH:27][C:28]([O:31][C:32]([F:35])([F:33])[F:34])=[CH:29][CH:30]=1)=[O:23])[CH3:37]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 86594050HCID 86594050, Verbindung

Produkt 1

HCID 102552732-{6-[1-Ethyl-3-(4-trifluoromethoxyphenyl)ureido]-5,6,7,8-tetrahydronaphthalen-2-ylsulfanyl}-2-methylpropionic acidAusbeute 43,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To 2-{6-[1-ethyl-3-(4-trifluoromethoxyphenyl)ureido]-5,6,7,8-tetrahydronaphthalen-2-ylsulfanyl}-2-methylpropionic acid tert butyl ester (1.66 g; 3.0 mmol) dissolved in CH2Cl2 (15 mL) is added TFA (15 mL) and the reaction was stirred at RT for 1.5 h. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (SiO2) eluting with a hexanes-EtOAc gradient to afford 0.643 g (43%) of 2-{6-[1-ethyl-3-(4-trifluoromethoxyphenyl)ureido]-5,6,7,8-tetrahydronaphthalen-2-ylsulfanyl}-2-methylpropionic acid as a white solid.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-e456e71ddb364ee8b5b1728892904a45
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07351857B2

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