Hydrochloric Acid → 4-[1-Pentyl-3-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoic Acid

HRID 1759782Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1759782
[CH2:1]([N:6]([C:24]1[CH:33]=[CH:32][C:27]([C:28]([O:30]C)=[O:29])=[CH:26][CH:25]=1)[C:7]([NH:9][C:10]1[CH:19]=[CH:18][C:17]2[C:16]([CH3:21])([CH3:20])[CH2:15][CH2:14][C:13]([CH3:23])([CH3:22])[C:12]=2[CH:11]=1)=[O:8])[CH2:2][CH2:3][CH2:4][CH3:5].O.[OH-].[Li+].Cl>C1COCC1.CO.O>[CH2:1]([N:6]([C:24]1[CH:25]=[CH:26][C:27]([C:28]([OH:30])=[O:29])=[CH:32][CH:33]=1)[C:7]([NH:9][C:10]1[CH:19]=[CH:18][C:17]2[C:16]([CH3:21])([CH3:20])[CH2:15][CH2:14][C:13]([CH3:22])([CH3:23])[C:12]=2[CH:11]=1)=[O:8])[CH2:2][CH2:3][CH2:4][CH3:5]

Komponenten

7

Edukt 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 22600038Methyl 4-[1-pentyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoate

Produkt 1

HCID 101602244-[1-Pentyl-3-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoic AcidAusbeute 40,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of methyl 4-[1-pentyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoate (190 mg) in 20 mL THF, 5 mL methanol 5 mL water was treated with lithium hydroxide hydrate (0.3 g) and stirred at room temperature for two hours. The mixture was diluted with 20 mL water, the pH adjusted to 2 with concentrated HCl and extracted with three 25 mL portions of ethyl acetate. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo, to give a pale yellow solid. The product was purified by flash chromatography (SiO2, 10% methanol/dichloromethane), to yield 75 mg of 4-[1-pentyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoic acid (42) as a white solid. M.P.: 201-202° C.

Aufarbeitung

  1. extractionextracted with three 25 mL portions of ethyl acetate
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a pale yellow solid
  6. customThe product was purified by flash chromatography (SiO2, 10% methanol/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-6ac8b75ef90040c19f9c2db2f50483b3
Quelldatensatz
uspto-grants-2005_01
Patentnummer
US06838472B2

Notizen zur Reaktion

Wird geladen…