Sodium Hydroxide → HCID 178431925, Verbindung

HRID 1764379Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1764379
[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.[OH-].[Na+].[N:19]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:29][C:30](O)=[O:31])=[N+:20]=[N-:21].Cl.CN(C)CCCN=C=NCC>O1CCCC1.O>[N:19]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:29][C:30]([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:31])=[N+:20]=[N-:21]

Komponenten

6

Edukt 4

HCID 14798Sodium HydroxideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 3016229(2-(Azidomethyl)phenyl)acetic acidHCID 178431949HCID 178431949, Verbindung

Produkt 1

HCID 178431925HCID 178431925, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

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

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A stirred suspension of 21.73 g. of 6-amino-2,2-dimethyl-3-(5-tetrazolyl)penam in 400 ml. of a 50:50 mixture of tetrahydrofuran-water is cooled to ca. 0° C. and the pH is adjusted to 7.5 using 1.0N sodium hydroxide. To the solution thus obtained, is added 17.3 g. of 2-(2-azidomethylphenyl)acetic acid (U.S. Pat. No. 3,766,175), followed by 17.4 g. of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride. The pH drops to 5.5. The reaction mixture is then stirred at ambient temperature, at pH 6, for 3 hours. At this point, the bulk of the tetrahydrofuran is removed by evaporation in vacuo, and the residual aqueous phase is extracted with ethyl acetate. The organic extract is discarded and the aqueuos phase is cooled to ca. 0° C. The pH is then adjusted to 2 and the product is extracted into ethyl acetate. The ethyl acetate is dried and evaporated, leaving 34.8 g. of the title compound as a tan solid. IR(CHCl3) 2100, 1790, 1680 and 1515 cm.-1NMR (DMSO-d6): 7.37 (s, 4H), 5.60 (m, 2H), 5.23 (s, 1H), 4.55 (s, 2H), 3.70 (s, 2H), 1.66 (s, 3H) and 1.06 ppm (s, 3H).

Aufarbeitung

  1. additionA stirred suspension of 21.73 g
  2. customTo the solution thus obtained
  3. additionis added 17.3 g
  4. customAt this point, the bulk of the tetrahydrofuran is removed by evaporation in vacuo
  5. extractionthe residual aqueous phase is extracted with ethyl acetate
  6. extractionThe organic extract
  7. temperaturethe aqueuos phase is cooled to ca. 0° C
  8. extractionthe product is extracted into ethyl acetate
  9. dry with materialThe ethyl acetate is dried
  10. customevaporated
  11. customleaving 34.8 g

Quellen und Nachweise

ORD-Eintrag
ord-1942deb3eb2647b48a23013105664629
Quelldatensatz
uspto-grants-1978_09
Patentnummer
US04115385

Notizen zur Reaktion

Wird geladen…