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Phosphorus pentachloride → 7-[2-Ethoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate

HRID 1163879
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Reaktionsgleichung

Reaktionsgleichung von HRID 1163879
[CH2:1]([O:3][N:4]=[C:5]([C:9]1[N:10]=[C:11]([NH:14][CH:15]=[O:16])[S:12][CH:13]=1)[C:6]([OH:8])=O)[CH3:2].P(Cl)(Cl)(Cl)(Cl)Cl.C[Si](C)(C)NC(=O)C.O.O.Cl.[Cl-].[NH2:35][CH:36]1[C:53](=[O:54])[N:38]2[C:39]([C:50]([OH:52])=[O:51])=[C:40]([CH2:43][N+:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[CH2:41][S:42][C@H:37]12>ClCCl.O1CCCC1.C(OCC)(=O)C.O.C(N(CC)CC)C>[CH2:1]([O:3][N:4]=[C:5]([C:9]1[N:10]=[C:11]([NH:14][CH:15]=[O:16])[S:12][CH:13]=1)[C:6]([NH:35][CH:36]1[C:53](=[O:54])[N:38]2[C:39]([C:50]([O-:52])=[O:51])=[C:40]([CH2:43][N+:44]3[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=3)[CH2:41][S:42][C@H:37]12)=[O:8])[CH3:2]
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Komponenten

10

Edukt 4

HCID 24819Phosphorus pentachlorideHCID 25989Acetamide, N-(trimethylsilyl)-HCID 544580772-(2-Formamidothiazol-4-yl)-2-ethoxyiminoacetic acidHCID 70450238HCID 70450238, Verbindung

Produkt 1

HCID 1317129237-[2-Ethoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylateAusbeute 39,3 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2-Ethoxyimino-2-(2-formamidothiazol-4-yl)acetic acid (syn isomer) (2.2 g) was added to a solution of phosphorus pentachloride (2.0 g) in dichloromethane (40 ml) at -10° C., and stirred at -5° C. to -10° C. for 1 hour. After the addition of triethylamine (2.0 g), the resulting mixture was stirred at -5° C. for 5 minutes [Solution A]. N-trimethylsilylacetamide (9.8 g) was added to a stirred suspension of 1-[(7-amino-4-carboxy-3-cephem-3-yl)methyl]pyridinium chloride hydrochloride dihydrate (3.0 g) in dry tetrahydrofuran (60 ml), and the mixture was stirred for 20 minutes at 35° C. to 40° C. To the solution was added the solution A at -10° C. and the resulting solution was stirred at the same temperature for 40 minutes. Water and ethyl acetate were added to the reaction mixture at -10° C. and the separated aqueous layer was washed with ethyl acetate and adjusted to pH 4.0 with 10% aqueous solution of sodium hydroxide. The resulting solution was subjected to column chromatography on macroporous non-ionic adsorption resin "Diaion HP-20" (Trademark: Prepared by Mitsubishi Chemical Industries) and eluted with 10% aqueous solution of isopropyl alcohol. The fractions containing the object compound were collected and concentrated and lyophilized to give 7-[2-ethoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate (syn isomer) (1.52 g).

Aufarbeitung

  1. stirringthe mixture was stirred for 20 minutes at 35° C. to 40° C
  2. stirringthe resulting solution was stirred at the same temperature for 40 minutes
  3. washthe separated aqueous layer was washed with ethyl acetate
  4. customThe resulting solution was subjected to column chromatography on macroporous non-ionic adsorption resin "Diaion HP-20" (Trademark: Prepared by Mitsubishi Chemical Industries)
  5. washeluted with 10% aqueous solution of isopropyl alcohol
  6. additionThe fractions containing the object compound
  7. customwere collected
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c95f5b576d244dff86f896a36031c7bf
Quelldatensatz
uspto-grants-1983_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04367228

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