Methanol → 7-(2-Methoxyimino-3,3-diethoxy-4-chlorobutyramido)-3-hydroxycepham-4-carboxylic acid

HRID 1982057Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1982057
CO.[NH2:3][CH:4]1[C:15](=[O:16])[N:6]2[CH:7]([C:12]([OH:14])=[O:13])[CH:8]([OH:11])[CH2:9][S:10][C@H:5]12.C(=O)(O)[O-].[Na+].[CH3:22][O:23][N:24]=[C:25]([C:29]([O:35][CH2:36][CH3:37])([O:32][CH2:33][CH3:34])[CH2:30][Cl:31])[C:26](Cl)=[O:27]>O.O1CCCC1>[CH3:22][O:23][N:24]=[C:25]([C:29]([O:35][CH2:36][CH3:37])([O:32][CH2:33][CH3:34])[CH2:30][Cl:31])[C:26]([NH:3][CH:4]1[C:15](=[O:16])[N:6]2[CH:7]([C:12]([OH:14])=[O:13])[CH:8]([OH:11])[CH2:9][S:10][C@H:5]12)=[O:27]

Komponenten

7

Edukt 4

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 13072520(6R)-7-amino-3-hydroxy-8-oxo-5-thia-1-azabicyclo[4.2.0]octane-2-carboxylic acidHCID 543636652-Methoxyimino-3,3-diethoxy-4-chlorobutyryl chloride

Produkt 1

HCID 867388377-(2-Methoxyimino-3,3-diethoxy-4-chlorobutyramido)-3-hydroxycepham-4-carboxylic acidAusbeute 132,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Methanol (40 ml) was added to a solution of 7-amino-3-hydroxycepham-4-carboxylic acid (2 g) and sodium bicarbonate (0.57 g) in water (13.4 g) under ice-cooling. A solution of 2-methoxyimino-3,3-diethoxy-4-chlorobutyryl chloride (syn isomer, 1.34 g) in dry tetrahydrofuran (2 ml) was added to a solution while adjusting pH 6.5 to 7.8, then and stirred under ice-cooling for three hours. After adjusting the resultant mixture to pH 7.5, the solvent was removed in vacuo. The aqueous residue was adjusted to pH 7.5 under ice-cooling, and diisopropyl ether (10 ml) was added to the solution. After the aqueous solution was separated, ethyl acetate (20 ml) was added to the aqueous solution, and adjusted to pH 2.0 with 20% sulfuric acid. The ethyl acetate layer was separated and the aqueous solution was extracted with ethyl acetate (10 ml) twice. The ethyl acetate layer and the extract were combined, washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The solution was concentrated in vacuo to give 7-(2-methoxyimino-3,3-diethoxy-4-chlorobutyramido)-3-hydroxycepham-4-carboxylic acid (syn isomer, 2.97 g).

Aufarbeitung

  1. temperaturecooling
  2. temperaturecooling for three hours
  3. customthe solvent was removed in vacuo
  4. temperaturecooling
  5. additiondiisopropyl ether (10 ml) was added to the solution
  6. customAfter the aqueous solution was separated
  7. additionethyl acetate (20 ml) was added to the aqueous solution
  8. customThe ethyl acetate layer was separated
  9. extractionthe aqueous solution was extracted with ethyl acetate (10 ml) twice
  10. washwashed with a saturated aqueous solution of sodium chloride
  11. dry with materialdried over magnesium sulfate
  12. concentrationThe solution was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-159cc4e467a2423abcae523b711f736c
Quelldatensatz
uspto-grants-1986_06
Patentnummer
US04594446

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