Hydrochloric Acid → (RS)-3-[4-[1-(4-tert-Butylphenyl)-3-(4-trifluoromethoxyphenyl)ureidomethyl]benzoylamino}-2-hydroxypropionic Acid

HRID 412442Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 412442
C([O:3][C:4](=[O:43])[CH:5]([OH:42])[CH2:6][NH:7][C:8](=[O:41])[C:9]1[CH:14]=[CH:13][C:12]([CH:15]([NH:26][C:27]([NH:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][C:37]([F:40])([F:39])[F:38])=[CH:32][CH:31]=2)=[O:28])[C:16]2[CH:21]=[CH:20][C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:18][CH:17]=2)=[CH:11][CH:10]=1)C.[OH-].[Na+].Cl>C(O)C>[C:22]([C:19]1[CH:18]=[CH:17][C:16]([CH:15]([NH:26][C:27]([NH:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][C:37]([F:38])([F:39])[F:40])=[CH:32][CH:31]=2)=[O:28])[C:12]2[CH:13]=[CH:14][C:9]([C:8]([NH:7][CH2:6][CH:5]([OH:42])[C:4]([OH:43])=[O:3])=[O:41])=[CH:10][CH:11]=2)=[CH:21][CH:20]=1)([CH3:25])([CH3:23])[CH3:24]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 674831433-{4-[1-(4-Tert-butylphenyl)-3-(4-trifluoromethoxyphenyl)ureidomethyl]benzoylamino}-2-hydroxypropionic acid ethyl ester

Produkt 1

HCID 22311113(RS)-3-[4-[1-(4-tert-Butylphenyl)-3-(4-trifluoromethoxyphenyl)ureidomethyl]benzoylamino}-2-hydroxypropionic AcidAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 3-{4-[1-(4-tert-butylphenyl)-3-(4-trifluoromethoxyphenyl)ureidomethyl]benzoyl-amino}-2-hydroxypropionic acid ethyl ester was stirred in absolute ethanol (20 mL) and 1 M sodium hydroxide (6 mL) was added. Stirring was continued for 17 hours and the solution was acidified with aqueous hydrochloric acid. The solvent was decanted and the remaining oil was dissolved in acetonitrile (20 mL) by heating. Water (20 mL) was added dropwise under vigorous stirring and the mixture was allowed to cool to room temperature. The precipitate was filtered off, washed with water and dried to afford 0.51 g (43%) of the title compound as a solid.

Aufarbeitung

  1. customThe solvent was decanted
  2. dissolutionthe remaining oil was dissolved in acetonitrile (20 mL)
  3. temperatureby heating
  4. additionWater (20 mL) was added dropwise
  5. stirringunder vigorous stirring
  6. filtrationThe precipitate was filtered off
  7. washwashed with water
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-13ee7b9bb07a4bb593557c77ddee4182
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06562807B2

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