2-Methyl-2-butene → 5-(2-Acetamido-4-methylthiazol-5-yl)furan-2-carboxylic acid

HRID 2386176Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2386176
[CH:1]([C:3]1[O:7][C:6]([C:8]2[S:12][C:11]([NH:13][C:14](=[O:16])[CH3:15])=[N:10][C:9]=2[CH3:17])=[CH:5][CH:4]=1)=[O:2].P([O-])([O-])([O-])=[O:19].[Na+].[Na+].[Na+].CC(=CC)C.Cl([O-])=O.[Na+]>C(O)(C)(C)C.C1COCC1.O>[C:14]([NH:13][C:11]1[S:12][C:8]([C:6]2[O:7][C:3]([C:1]([OH:19])=[O:2])=[CH:4][CH:5]=2)=[C:9]([CH3:17])[N:10]=1)(=[O:16])[CH3:15]

Komponenten

8

Edukt 4

HCID 105532-Methyl-2-buteneHCID 24243Trisodium PhosphateHCID 14532745N-(5-(5-formylfuran-2-yl)-4-methylthiazol-2-yl)acetamideHCID 23668197Sodium Chlorite

Produkt 1

HCID 593622035-(2-Acetamido-4-methylthiazol-5-yl)furan-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel2×HCID 6386tert-ButanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 1.2 g of N-(5-(5-formylfuran-2-yl)-4-methylthiazol-2-yl)acetamide in 100 mL of tert-butanol was added 5 mL of water and 20 mL of 2N monobasic sodium phosphate. The resulting suspension was cooled to 0° C. while being stirred. To the chilled suspension was added 20 mL of a 2M solution of 2-methyl-2-butene in THF followed by 3 g of sodium chlorite in 10 mL of water. The reaction was allowed to warm to room temperature overnight and the upper organic layer was separated and dried over sodium sulfate and used as is in the subsequent reactions. LC/MS: 267.04 (M+H)/2.04 min.

Aufarbeitung

  1. temperatureto warm to room temperature overnight
  2. customthe upper organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. custom2.04 min.

Quellen und Nachweise

ORD-Eintrag
ord-6710a48b72e7496ab71fcbd1057c37c5
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08268818B2

Notizen zur Reaktion

Wird geladen…