Formic Acid → 2-(3-Pyridinyl)-3-formyl-5,5-dimethyl-4-thiazolidinecarboxylic acid

HRID 2210595Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2210595
[CH:1](O)=[O:2].C(OC(=O)C)(=O)C.[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]2[NH:21][CH:20]([C:22]([OH:24])=[O:23])[C:19]([CH3:26])([CH3:25])[S:18]2)[CH:12]=1>C1COCC1>[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]2[N:21]([CH:1]=[O:2])[CH:20]([C:22]([OH:24])=[O:23])[C:19]([CH3:26])([CH3:25])[S:18]2)[CH:12]=1

Komponenten

5

Edukt 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 27377735,5-Dimethyl-2-(pyridin-3-yl)-1,3-thiazolidine-4-carboxylic acid

Produkt 1

HCID 133392752-(3-Pyridinyl)-3-formyl-5,5-dimethyl-4-thiazolidinecarboxylic acidAusbeute 89,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Formic acid (17 g, 378 mmol) and acetic anhydride (13 g, 126 mmol) where combined at 10° C. A slurry of 2-(3-pyridinyl)-5,5-dimethyl-4-thiazolidinecarboxylic acid (10 g, 42 mmol), Prepared as in step 1, in THF (250 mL) was added over five minutes. The resulting clear-yellow solution was wanted slowly to ambient temperature and stirred for 17 hours, during which time it became a white suspension. The THF was removed in vacuo, and the resulting slurry was filtered to yield a white solid. The solid was rinsed with ether to give 2-(3-pyridinyl)-3-formyl-5,5-dimethyl-4-thiazolidinecarboxylic acid (10 g) which was used without further purification.

Aufarbeitung

  1. customcombined at 10° C
  2. customwas wanted slowly to ambient temperature
  3. customThe THF was removed in vacuo
  4. filtrationthe resulting slurry was filtered
  5. customto yield a white solid
  6. washThe solid was rinsed with ether

Quellen und Nachweise

ORD-Eintrag
ord-3cc584431e97481392905d246e6a8390
Quelldatensatz
uspto-grants-1995_10
Patentnummer
US05459152

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