Tetrahydrofuran → Ceftiofur

HRID 271803

Reaktionsgleichung

Reaktionsgleichung von HRID 271803
[NH2:1][C:2]([NH2:4])=[S:3].Br[CH2:6][C:7](=O)/[C:8](=[N:33]/[O:34][CH3:35])/[C:9]([NH:11][CH:12]1[C:31](=[O:32])[N:14]2[C:15]([C:28]([OH:30])=[O:29])=[C:16]([CH2:19][S:20][C:21]([C:23]3[O:24][CH:25]=[CH:26][CH:27]=3)=[O:22])[CH2:17][S:18][C@H:13]12)=[O:10].O1CCCC1.C(=O)(O)[O-].[Na+]>O.C(Cl)Cl>[CH3:35][O:34]/[N:33]=[C:8](\[C:9]([NH:11][C@@H:12]1[C:31](=[O:32])[N:14]2[C:15]([C:28]([OH:30])=[O:29])=[C:16]([CH2:19][S:20][C:21]([C:23]3[O:24][CH:25]=[CH:26][CH:27]=3)=[O:22])[CH2:17][S:18][C@H:13]12)=[O:10])/[C:7]1[N:1]=[C:2]([NH2:4])[S:3][CH:6]=1

Komponenten

7

Edukt 4

HCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 2723790ThioureaHCID 177711896(6R)-7-[[(2Z)-4-bromo-2-methoxyimino-3-oxobutanoyl]amino]-3-(furan-2-carbonylsulfanylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Produkt 1

HCID 6328657Ceftiofur

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
7.5 °C

Versuchsvorschrift

25.0 g (0.3289 moles) of thiourea was dissolved in 160 ml of demineralised water. This solution was added to a mixture containing 7-[4-bromo-2(Z)-methoxyimino-3-oxobutyramido]-3-[[(2-furanylcarbonyl)thio]methyl]-3-cephem-4-carboxylic acid in methylene chloride, as obtained from Step C 240 ml of tetrahydrofuran (THF) over a period of 30 mins. The reaction mixture was stirred for 2 hrs at 5-10° C. The pH of the solution was adjusted to 5.0 with aqueous sodium bicarbonate solution.

Aufarbeitung

  1. additionThis solution was added to a mixture

Quellen und Nachweise

ORD-Eintrag
ord-acfb1b4f13ca4b44b9b3dad769dd056c
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452990B2

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