Sulfuric Acid → [2-(6-Chloro-pyridin-3-yl)-5-methyl-oxazol-4-yl]-acetic acid methyl ester

HRID 854550

Reaktionsgleichung

Reaktionsgleichung von HRID 854550
[CH3:1][O:2][C:3](=[O:19])[CH2:4][CH:5]([NH:9][C:10]([C:12]1[CH:13]=[N:14][C:15]([Cl:18])=[CH:16][CH:17]=1)=[O:11])[C:6](=O)[CH3:7].S(=O)(=O)(O)O>C(OC(=O)C)(=O)C>[CH3:1][O:2][C:3](=[O:19])[CH2:4][C:5]1[N:9]=[C:10]([C:12]2[CH:13]=[N:14][C:15]([Cl:18])=[CH:16][CH:17]=2)[O:11][C:6]=1[CH3:7]

Komponenten

4

Edukt 2

HCID 1118Sulfuric AcidHCID 877132023-[(6-Chloro-pyridine-3-carbonyl)-amino]-4-oxo-pentanoic acid methyl ester

Produkt 1

HCID 58765666[2-(6-Chloro-pyridin-3-yl)-5-methyl-oxazol-4-yl]-acetic acid methyl esterAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7918Acetic AnhydrideLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

3-[(6-Chloro-pyridine-3-carbonyl)-amino]-4-oxo-pentanoic acid methyl ester is dissolved in acetic anhydride (75 mL) and concentrated sulfuric acid is added in 500 uL portions five times over a four hour period. The reaction is monitored by HPLC. The reaction is then heated to 40° C. until the starting material is consumed. The reaction is allowed to proceed at room temperature overnight. The reaction is then concentrated to dryness and purified by column chromatography. This procedure yielded (12.8 g, 48 mmol) 22% of the desired oxazole over four steps.

Aufarbeitung

  1. customis consumed
  2. concentrationThe reaction is then concentrated to dryness
  3. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-973361e0cb97477593554eef8b429eaa
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07259175B2

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