4-Methylmorpholine → HCID 131717474, Verbindung

HRID 655056

Reaktionsgleichung

Reaktionsgleichung von HRID 655056
[CH3:1][O:2][C:3]1[CH:33]=[CH:32][C:6]([CH2:7][O:8][C:9]([C:11]2[N:16]3[C:17](=[O:29])[C@@H:18]([NH:19]C(=O)CC4C=CC=CC=4)[C@H:15]3[S:14][CH2:13][C:12]=2[CH2:30][Cl:31])=[O:10])=[CH:5][CH:4]=1.CN1[CH2:40][CH2:39]OCC1.[C:41]([O:45][C:46]([NH:48][C:49]1[S:50][CH:51]=[C:52]([C:54](=[N:58][O:59][CH2:60][C:61](OC(C)(C)C)=O)[C:55]([OH:57])=O)[N:53]=1)=[O:47])([CH3:44])([CH3:43])[CH3:42].[CH:68]1[CH:73]=[CH:72][C:71](OP(Cl)(Cl)=O)=[CH:70][CH:69]=1>ClCCl.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]([C:11]2[N:16]3[C:17](=[O:29])[C@@H:18]([NH:19][C:55](=[O:57])[C:54]([C:52]4[N:53]=[C:49]([NH:48][C:46]([O:45][C:41]([CH3:42])([CH3:43])[CH3:44])=[O:47])[S:50][CH:51]=4)=[N:58][O:59][C:60]([C:61]4[CH:40]=[CH:39][CH:12]=[CH:11][CH:9]=4)([C:3]4[CH:33]=[CH:32][CH:6]=[CH:5][CH:4]=4)[C:68]4[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=4)[C@H:15]3[S:14][CH2:13][C:12]=2[CH2:30][Cl:31])=[O:10])=[CH:32][CH:33]=1

Komponenten

7

Edukt 4

HCID 79724-Methylmorpholine2×HCID 13038Phosphorodichloridic acid, phenyl esterHCID 10874591(4-Methoxyphenyl)methyl (6R,7R)-3-(chloromethyl)-8-oxo-7-((2-phenylacetyl)amino)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylateHCID 53716865HCID 53716865, Verbindung

Produkt 1

HCID 131717474HCID 131717474, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
-40 °C

Versuchsvorschrift

To a suspension of 7β-amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester (1) toluene-p-sulfonic acid salt (3.94 g; (7.28 mMol.) in dichloromethane (50 ml) keeping at 0° C. are added N-methylmorpholin (0.80 ml; 1 Eq.) and 2-(2-t-butoxycarbonylamino-4-thiazolyl)-2-t-butoxycarbonylmethoxyiminoacetic acid (3.80 g; 1.3 Eq.) and cooled at -40° C. To this mixture are added phenylphosphoric acid dichloride (1.41 ml; 1.3 Eq.) and N-methylmorpholin (2.41 ml; 3 Eq.), and the mixture is stirred at -40° to -15° C. for 1.5 hours. The reaction mixture is diluted with ethyl acetate, washed with water, diluted hydrochloric acid and water, dried, and concentrated under reduced pressure. The residue is purified by silica gel chromatography (toluene toluene: ethyl acetate) to give 7β-[2-(2-t-butoxycarbonylamino-4-thiazolyl)-2-t-butoxycarbonylmethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester (2) (5.20 g).

Aufarbeitung

  1. customkeeping at 0° C.
  2. washwashed with water, diluted hydrochloric acid and water
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by silica gel chromatography (toluene toluene: ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-871313f628f1425fba0d1c59af88520e
Quelldatensatz
uspto-grants-1992_07
Patentnummer
US05134138

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