Ethyl Acetate → HCID 21891719, Verbindung

HRID 720668Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 720668
C([O:3][C:4]([C:6]1[S:10][C:9]([NH:11][C:12]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:8][C:7]=1[CH3:31])=[O:5])C.[OH-].[Na+].C(OCC)(=O)C>C(O)C.O>[CH3:31][C:7]1[N:8]=[C:9]([NH:11][C:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[S:10][C:6]=1[C:4]([OH:5])=[O:3]

Komponenten

6

Edukt 3

HCID 8857Ethyl AcetateHCID 14798Sodium Hydroxide2×HCID 58739232HCID 58739232, Verbindung

Produkt 1

HCID 21891719HCID 21891719, VerbindungAusbeute 11,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of 4-methyl-2-(trityl-amino)-thiazole-5-carboxylic acid ethyl ester (500 mg, 1.17 mmol) in ethanol (10 mL) at 25° C. was treated with a 1N aqueous sodium hydroxide solution (3.51 mL, 3.51 mmol). The resulting mixture was heated to 50° C. for 18 h. At this time, the reaction was treated with an additional amount of a 1N aqueous sodium hydroxide solution (3.6 mL, 3.6 mmol). This mixture was heated at 50° C. for an additional 8 days. At this time, the reaction was diluted with water (100 mL), acidified to pH=5, and treated with ethyl acetate. The resulting white solid was collected by filtration and dried in vacuo. The filtrate was extracted with ethyl acetate. The organics were dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 4-methyl-2-(trityl-amino)-thiazole-5-carboxylic acid (55.7 mg, 11.9%) as a white solid: 1H NMR (DMSO-d6, 300 MHz) δ9.09 (broad s, 1H), 7.22 (m, 15 H), 2.22 (s, 3H).

Aufarbeitung

  1. temperatureThis mixture was heated at 50° C. for an additional 8 days
  2. filtrationThe resulting white solid was collected by filtration
  3. customdried in vacuo
  4. extractionThe filtrate was extracted with ethyl acetate
  5. dry with materialThe organics were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-02a5209054e24bbf8939a90205d1be0d
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07135475B2

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