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7-Amino-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid → 7-tert.-Butoxycarbonylamino-2-carboxy-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene

HRID 1660390
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1660390
[NH2:1][CH:2]1[C:9](=[O:10])[N:8]2[CH:3]1[S:4][CH2:5][C:6]([CH3:14])=[C:7]2[C:11]([OH:13])=[O:12].[C:15](=O)([O:21]C(C)(C)C)[O:16][C:17]([CH3:20])([CH3:19])[CH3:18]>C(=O)(O)[O-].[Na+].O.O1CCOCC1>[C:17]([O:16][C:15]([NH:1][CH:2]1[C:9](=[O:10])[N:8]2[CH:3]1[S:4][CH2:5][C:6]([CH3:14])=[C:7]2[C:11]([OH:13])=[O:12])=[O:21])([CH3:20])([CH3:19])[CH3:18]
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Komponenten

6

Edukt 2

HCID 18837-Amino-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acidHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Produkt 1

HCID 128967587-tert.-Butoxycarbonylamino-2-carboxy-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-eneAusbeute 89,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel
HCID 31275
1,4-Dioxane
Lösungsmittel
2×
HCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

7-Amino-2-carboxy-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (371 g) is dissolved in a solution of sodium bicarbonate (307 g) in a mixture of distilled water (2 liters) and dioxane (2 liters). A solution of di-tert.-butyl carbonate (421 g) in dioxane (2 liters) is added in the course of 10 minutes. The reaction mixture is stirred for 48 hours at 25° C. The suspension obtained is concentrated under reduced pressure (20 mm Hg) at 50° C. to a residual volume of about 2 liters, and is then diluted with ethyl acetate (1 liter) and distilled water (2 liters). The aqueous phase is decanted, washed with ethyl acetate (500 cc) and acidified to pH 2 with 6 N hydrochloric acid in the presence of ethyl acetate (1500 cc). The aqueous phase is extracted with ethyl acetate (2×1 liter). The combined organic phases are washed with a saturated sodium chloride solution (2×250 cc) and dried over sodium sulphate. After filtration, the solvent is evaporated under reduced pressure (20 mm Hg) at 50° C. 7-tert.-Butoxycarbonylamino-2-carboxy-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (486 g) is obtained in the form of yellow crystals (m.p.=190° C., with decomposition).

Aufarbeitung

  1. customThe suspension obtained
  2. concentrationis concentrated under reduced pressure (20 mm Hg) at 50° C. to a residual volume of about 2 liters
  3. additionis then diluted with ethyl acetate (1 liter)
  4. distillationdistilled water (2 liters)
  5. customThe aqueous phase is decanted
  6. washwashed with ethyl acetate (500 cc)
  7. extractionThe aqueous phase is extracted with ethyl acetate (2×1 liter)
  8. washThe combined organic phases are washed with a saturated sodium chloride solution (2×250 cc)
  9. dry with materialdried over sodium sulphate
  10. filtrationAfter filtration
  11. customthe solvent is evaporated under reduced pressure (20 mm Hg) at 50° C

Quellen und Nachweise

ORD-Eintrag
ord-7034206d02f2485c8963423f3e79dc86
Quelldatensatz
uspto-grants-1981_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04307230

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