Dicyclohexylcarbodiimide → HCID 21454862, Verbindung

HRID 435961Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 435961
[C:1]([O:4][CH2:5][C:6]1[CH2:13][S:12][CH:11]2[N:8]([C:9](=[O:15])[CH:10]2[NH2:14])[C:7]=1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])(=[O:3])[CH3:2].C1(N=C=NC2CCCCC2)CCCCC1.[S:38]1[CH2:43][CH2:42][S:41][CH:40]=[C:39]1[CH2:44][C:45](O)=[O:46]>CN(C)C=O>[C:1]([O:4][CH2:5][C:6]1[CH2:13][S:12][CH:11]2[N:8]([C:9](=[O:15])[CH:10]2[NH:14][C:45](=[O:46])[CH2:44][C:39]2[S:38][CH2:43][CH2:42][S:41][CH:40]=2)[C:7]=1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 11771800HCID 11771800, VerbindungHCID 21454861HCID 21454861, Verbindung

Produkt 1

HCID 21454862HCID 21454862, VerbindungAusbeute 62,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

3-Acetoxymethyl-7-amino-2(t-butoxycarbonyl)-8-oxo-5-thia-1-aza-bicyclo[4,2,0]oct-2-ene (11.2 g.) and dicyclohexylcarbodiimide (7.8 g.) are added to a solution of (5,6-dihydro-1,4-dithiin-2-yl)acetic acid (6 g.) in dimethylformamide (50 cc.). The reagents are left in contact for 5 hours, with stirring, at a temperature of about 20° C. and then the solid is filtered off. The filtrate is taken up in ethyl acetate (300 cc.) and is washed with an aqueous solution of sodium bicarbonate, N hydrochloric acid and then with water. After drying over sodium sulphate, it is treated with decolourizing charcoal and concentrated to dryness under reduced pressure (20 mm.Hg). A residue (20 g.) is obtained and is chromatographed on silica (330 g.). Elution is effected using a mixture (10 liters) of ethyl acetate and cyclohexane (1-3 by volume), and the eluates are concentrated to dryness under reduced pressure (20 mm.Hg). 3-Acetoxymethyl-2-(t-butoxycarbonyl)-7-[(5,6-dihydro-1,4-dithiin-2 -yl)acetamido]-8-oxo-5-thia-1 -aza-bicyclo-[4,2,0]oct-2-ene (10.3 g.), melting at 80° C., is thus obtained.

Aufarbeitung

  1. filtrationthe solid is filtered off
  2. washis washed with an aqueous solution of sodium bicarbonate, N hydrochloric acid
  3. dry with materialAfter drying over sodium sulphate, it
  4. additionis treated with decolourizing charcoal
  5. concentrationconcentrated to dryness under reduced pressure (20 mm.Hg)
  6. customA residue (20 g.) is obtained
  7. customis chromatographed on silica (330 g.)
  8. washElution
  9. concentrationthe eluates are concentrated to dryness under reduced pressure (20 mm.Hg)

Quellen und Nachweise

ORD-Eintrag
ord-1cded7211a68421194c57c6f2de43517
Quelldatensatz
uspto-grants-1977_02
Patentnummer
US04007176

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