Water → HCID 49833752, Verbindung

HRID 1614864Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1614864
[O:1]=[C:2]1[CH2:6][CH2:5][C@@H:4]([C:7]2[CH:17]=[CH:16][C:10]([O:11][CH2:12][C:13](O)=[O:14])=[CH:9][CH:8]=2)[CH2:3]1.C1N=C[N:20](C(N2C=NC=C2)=O)C=1.[OH-].[NH4+].O>CN(C=O)C>[O:1]=[C:2]1[CH2:6][CH2:5][C@@H:4]([C:7]2[CH:17]=[CH:16][C:10]([O:11][CH2:12][C:13]([NH2:20])=[O:14])=[CH:9][CH:8]=2)[CH2:3]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 49834134HCID 49834134, Verbindung

Produkt 1

HCID 49833752HCID 49833752, VerbindungAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

(R)-[4-(3-Oxo-cyclopentyl)-phenoxy]-acetic acid (preparation 31) (1.6 mmol, 375 mg) was dissolved in DMF (3 mL), then CDI (1.84 mmol, 299 mg) was added and the reaction mixture stirred at r.t. for 90 min. Ammonium hydroxide (25% aq, 7 mL) was added and a precipitate formed. Water (7 mL) was added and the precipitate filtered off and dried in vacuo to yield the title compound (302 mg, 81%). 1H NMR (300 MHz, CDCl3) δ 7.25-7.14 (m, 2H), 6.97-6.83 (m, 2H), 6.78 (bs, 1H), 5.91 (bs, 1H), 4.49 (s, 2H), 3.52-3.28 (m, 1H), 2.77-2.57 (m, 1H), 2.57-2.11 (m, 5H), 2.09-1.79 (m, 1H).

Aufarbeitung

  1. customa precipitate formed
  2. filtrationthe precipitate filtered off
  3. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1415293e8d88416fb053ee83379b3393
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765676B2

Notizen zur Reaktion

Wird geladen…