Hydrochloric Acid → 2-t-Butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetic acid

HRID 648835Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 648835
[S:1]1[CH:5]=[C:4]([C:6](=O)[C:7]([OH:9])=[O:8])[N:3]=[CH:2]1.[NH2:11][O:12][CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].C(=O)(O)[O-].[Na+].Cl.[Cl-].[Na+]>CO.O.C(OCC)(=O)C>[C:17]([O:16][C:14]([CH2:13][O:12][N:11]=[C:6]([C:4]1[N:3]=[CH:2][S:1][CH:5]=1)[C:7]([OH:9])=[O:8])=[O:15])([CH3:20])([CH3:19])[CH3:18]

Komponenten

9

Edukt 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 516892Sodium BicarbonateHCID 12919121tert-Butyl (aminooxy)acetateHCID 13187915HCID 13187915, Verbindung

Produkt 1

HCID 544727372-t-Butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetic acidAusbeute 66,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 2-(4-thiazolyl)glyoxylic acid (2.3 g) in methanol (23 ml) and t-butyl 2-aminooxyacetate (2.6 g) was stirred for an hour at ambient temperature. The reaction mixture was added to a mixture of ethyl acetate and water and adjusted to pH 7.5 with saturated aqueous solution of sodium bicarbonate. The separated aqueous layer was adjusted to pH 2.0 with 10% hydrochloric acid and the mixture was saturated sodium chloride. The acidic mixture was extracted with ethyl acetate. The extract layer was washed with saturated aqueous solution of sodium chloride, dried over magnesium sulfate and evaporated to give 2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetic acid (syn isomer) (2.8 g), mp. 136°-139° C.

Aufarbeitung

  1. extractionThe acidic mixture was extracted with ethyl acetate
  2. washThe extract layer was washed with saturated aqueous solution of sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-217fe107818444d2a981050eb046e194
Quelldatensatz
uspto-grants-1988_04
Patentnummer
US04736039

Notizen zur Reaktion

Wird geladen…