Hydrochloric Acid → 1-(3-methylbutyryloxy)-2-methylpropyl 7beta-amino-3-[[[1-(2-dimethylaminoethyl)-1H-tetrazol-5-yl]thio]methyl]ceph-3-em-4-carboxylate dihydrochloride

HRID 4260Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 4260
[ClH:1].Cl.[NH2:3][C@@H:4]1[C:26](=[O:27])[N:6]2[C:7]([C:23]([OH:25])=[O:24])=[C:8]([CH2:11][S:12][C:13]3[N:17]([CH2:18][CH2:19][N:20]([CH3:22])[CH3:21])[N:16]=[N:15][N:14]=3)[CH2:9][S:10][C@H:5]12.C([O-])(=O)C.[K+].[CH3:33][CH:34]([CH3:44])[CH2:35][C:36]([O:38][CH:39](I)[CH:40]([CH3:42])[CH3:41])=[O:37].Cl>C(Cl)Cl.CN(C)C=O>[ClH:1].[ClH:1].[NH2:3][C@@H:4]1[C:26](=[O:27])[N:6]2[C:7]([C:23]([O:25][CH:39]([O:38][C:36](=[O:37])[CH2:35][CH:34]([CH3:44])[CH3:33])[CH:40]([CH3:42])[CH3:41])=[O:24])=[C:8]([CH2:11][S:12][C:13]3[N:17]([CH2:18][CH2:19][N:20]([CH3:22])[CH3:21])[N:16]=[N:15][N:14]=3)[CH2:9][S:10][C@H:5]12

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 517044Potassium AcetateHCID 140301271-Iodo-2-methylpropyl 3-methylbutyrateHCID 703953067beta-amino-3-[[[1-(2-dimethylaminoethyl)-1H-tetrazol-5-yl]thio]methyl]ceph-3-em-4-carboxylic acid dihydrochloride

Produkt 1

HCID 704087121-(3-methylbutyryloxy)-2-methylpropyl 7beta-amino-3-[[[1-(2-dimethylaminoethyl)-1H-tetrazol-5-yl]thio]methyl]ceph-3-em-4-carboxylate dihydrochlorideAusbeute 106 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To 60 ml of dimethylformamide solution containing 4.22 g of 7β-amino-3-[[[1-(2-dimethylaminoethyl)-1H-tetrazol-5-yl]thio]methyl]ceph-3-em-4-carboxylic acid dihydrochloride is added 1.67 g of potassium acetate. The mixture is cooled to 0° C. With stirring, 5.0 g of 1-iodo-2-methylpropyl 3-methylbutyrate is added dropwise to the solution, followed by stirring at 0° C. for 5 minutes. The reaction mixture is poured into a mixture of 60 ml of methylene chloride and 60 ml of 0.1N-HCl and the aqueous layer is separated. The aqueous solution is adjusted to pH 6.0 with a saturated aqueous sodium bicarbonate solution and extracted with methylene chloride. To the methylene chloride solution is added water and the mixture is adjusted to pH 2.0 with 4N-HCl. The aqueous layer is separated and lyophilized to obtain 3.0 g of the title compound.

Aufarbeitung

  1. stirringby stirring at 0° C. for 5 minutes
  2. customthe aqueous layer is separated
  3. extractionextracted with methylene chloride
  4. additionTo the methylene chloride solution is added water
  5. customThe aqueous layer is separated

Quellen und Nachweise

ORD-Eintrag
ord-44f5f31ec6e3435b87b6de372f03caf8
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04725592

Notizen zur Reaktion

Wird geladen…