1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 6-(2-[3-Azidomethyl-2-thienyl]acetamido)-2,2-dimethyl-3-(5-tetrazolyl)penam

HRID 614149Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 614149
[NH2:1][CH:2]1[C:15](=[O:16])[N:4]2[CH:5]([C:10]3[NH:14][N:13]=[N:12][N:11]=3)[C:6]([CH3:9])([CH3:8])[S:7][C@H:3]12.[N:17]([CH2:20][C:21]1[CH:25]=[CH:24][S:23][C:22]=1[CH2:26][C:27](O)=[O:28])=[N+:18]=[N-:19].Cl.C(N=C=NCCCN(C)C)C>O1CCCC1.O>[N:17]([CH2:20][C:21]1[CH:25]=[CH:24][S:23][C:22]=1[CH2:26][C:27]([NH:1][CH:2]1[C:15](=[O:16])[N:4]2[CH:5]([C:10]3[NH:11][N:12]=[N:13][N:14]=3)[C:6]([CH3:8])([CH3:9])[S:7][C@H:3]12)=[O:28])=[N+:18]=[N-:19]

Komponenten

5

Edukt 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 203113693-Azidomethyl-2-thienylacetic AcidHCID 178431949HCID 178431949, Verbindung

Produkt 1

HCID 1784319296-(2-[3-Azidomethyl-2-thienyl]acetamido)-2,2-dimethyl-3-(5-tetrazolyl)penamAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21881883Oxolane--water (1/1)Lösungsmittel

Versuchsvorschrift

A solution of 5.48 g. (0.0228 mole) of 6-amino-2,2-dimethyl-3-(5-tetrazolyl)penam in 200 ml. of 1:1 tetrahydrofuran-water is adjusted to pH 7.5, and then 4.5 g. (0.0228 mole) of 2-(3-azidomethyl-2-thienyl)acetic acid is added. The mixture is cooled to 0°-5° C., and 4.37 g. (0.0288 mole) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride is added. The reaction mixture is stirred at pH 6 and at 0°-5° C. for 2.5 hours. At this point, the tetrahydrofuran is removed by evaporation in vacuo and the pH is adjusted to 7.5. The aqueous residue is washed with ethyl acetate and then the pH is lowered to 2.2. The product is extracted into ethyl acetate. The ethyl acetate is dried and evaporated in vacuo. This affords 8.1 g. (88% yield) of the title compound as a foam. IR (KBr disc): 2100, 1800, 1666, 1529 and 1250 cm -1. NMR (CDCl3): 7.3 (d, 1H), 7.0 (d, 1H), 5.7 (m, 2H), 5.3 (s, 1H), 4.4 (s, 2H), 3.9 (s, 2H), 1.6 (s, 3H) and 1.1 ppm (s, 3H).

Aufarbeitung

  1. temperatureThe mixture is cooled to 0°-5° C.
  2. customAt this point, the tetrahydrofuran is removed by evaporation in vacuo
  3. washThe aqueous residue is washed with ethyl acetate
  4. extractionThe product is extracted into ethyl acetate
  5. dry with materialThe ethyl acetate is dried
  6. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-78538731d3054c05987ccf315c21ca98
Quelldatensatz
uspto-grants-1979_03
Patentnummer
US04143039

Notizen zur Reaktion

Wird geladen…