Sodium Hydroxide → 2-Tert-butoxycarbonylmethoxyimino-2-(1,2,5-thiadiazol-3-yl)acetic acid
Reaktionsgleichung
[S:1]1[N:5]=[CH:4][C:3]([C:6](=O)[C:7]([OH:9])=[O:8])=[N:2]1.[C:11]([O:15][C:16]([CH2:18][O:19][NH2:20])=[O:17])([CH3:14])([CH3:13])[CH3:12].[OH-].[Na+]>O1CCCC1.O>[C:11]([O:15][C:16]([CH2:18][O:19][N:20]=[C:6]([C:3]1[CH:4]=[N:5][S:1][N:2]=1)[C:7]([OH:9])=[O:8])=[O:17])([CH3:14])([CH3:13])[CH3:12]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
To a solution of (1,2,5-thiadiazol-3-yl)glyoxylic acid (6 g) in tetrahydrofuran (30 ml) and water (30 ml) was added tert-butoxycarbonylmethoxyamine (8.37 g) at ambient temperature. The mixture was adjusted to pH 4.5-5.0 with 4N aqueous sodium hydroxide and stirred at ambient temperature for 4 hours. The mixture was adjusted to pH 7.5 with 4N aqueous sodium hydroxide and washed with ethyl acetate (100 ml×2). The aqueous solution was acidified to pH 2.0 with 10% hydrochloric acid and extracted with ethyl acetate (100 ml×2). The organic layer was washed with an aqueous sodium chloride and dried over magnesium sulfate. The solution was evaporated in vacuo to give 2-tert-butoxycarbonylmethoxyimino-2-(1,2,5-thiadiazol-3-yl)acetic acid (syn and anti mixture) (10.02 g).
Aufarbeitung
- washwashed with ethyl acetate (100 ml×2)
- extractionextracted with ethyl acetate (100 ml×2)
- washThe organic layer was washed with an aqueous sodium chloride
- dry with materialdried over magnesium sulfate
- customThe solution was evaporated in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-df38488b7e454b3bb34fad0e4d1dffcb
- Quelldatensatz
- uspto-grants-1984_08
- Patentnummer
- US04464369
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