Sodium Hydroxide → 2-(2-Benzoyl-phenylamino)-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-naphthalen-1-yl}-propionic acid

HRID 479128Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 479128
C([O:3][C:4](=[O:47])[CH:5]([NH:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[C:39](=[O:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([O:17][CH2:18][CH2:19][C:20]2[N:21]=[C:22]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[O:23][C:24]=2[CH3:25])=[CH:9][CH:8]=1)C.[OH-].[Na+]>C1COCC1.CCO>[C:39]([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=1[NH:32][CH:5]([CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([O:17][CH2:18][CH2:19][C:20]2[N:21]=[C:22]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[O:23][C:24]=2[CH3:25])=[CH:9][CH:8]=1)[C:4]([OH:47])=[O:3])(=[O:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 695571212-(2-Benzoyl-phenylamino)-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-naphthalen-1-yl}-propionic acid ethyl ester

Produkt 1

HCID 180034292-(2-Benzoyl-phenylamino)-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-naphthalen-1-yl}-propionic acidAusbeute 97,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21873804Tetrahydrofuran ethanolLösungsmittel

Versuchsvorschrift

0.213 g (0.341 mmol) of 2-(2-Benzoyl-phenylamino)-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-naphthalen-1-yl}-propionic acid ethyl ester was dissolved in 1.6 ml of THF/EtOH=1/1 and treated with 0.568 ml of 3N NaOH(5 eq). The reaction flask was stirred for 20 h at ambient temperature. The mixture was then poured onto crashed ice/NH4Cl, extracted twice with AcOEt, washed with brine, dried over sodium sulfate, and evaporated to dryness. Twofold crystallization from hexane/AcOEt yielded 0.199 g of the title product as yellow crystals of mp. 125° (dec.).

Aufarbeitung

  1. additionThe mixture was then poured
  2. extractionextracted twice with AcOEt
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness
  6. customTwofold crystallization from hexane/AcOEt

Quellen und Nachweise

ORD-Eintrag
ord-f2acfd50feca487c999732588a172213
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06642389B2

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