1,2-Dimethoxyethane → 7beta-Phenylacetamido-3-methoxy-ceph-2-em-4alpha-carboxylic acid diphenylmethyl ester

HRID 26109

Reaktionsgleichung

Reaktionsgleichung von HRID 26109
[C:1]1([CH:7]([O:14][C:15](=[O:47])/[C:16](/[N:21]2[CH:24]([S:25]S(C3C=CC(C)=CC=3)(=O)=O)[CH:23]([NH:36][C:37](=[O:45])[CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C:22]2=[O:46])=[C:17](\[O:19][CH3:20])/[CH3:18])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.COCCOC.N12CCCCC1C=NCCC2>C1(C)C=CC=CC=1>[C:8]1([CH:7]([O:14][C:15]([C@@H:16]2[N:21]3[C:22](=[O:46])[C@@H:23]([NH:36][C:37](=[O:45])[CH2:38][C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[C@H:24]3[S:25][CH:18]=[C:17]2[O:19][CH3:20])=[O:47])[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Komponenten

5

Edukt 3

HCID 80711,2-DimethoxyethaneHCID 3141121,5-Diazabicyclo(5,4,0)undec-5-eneHCID 705571822-[4-(p-Toluenesulphonylthio)-3-phenylacetamido-2-oxoazetidin-1-yl]-3-methoxy-crotonic acid diphenylmethyl ester

Produkt 1

HCID 704484817beta-Phenylacetamido-3-methoxy-ceph-2-em-4alpha-carboxylic acid diphenylmethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 670 mg (1 mmol) of 2-[4-(p-toluenesulphonylthio)-3-phenylacetamido-2-oxoazetidin-1-yl]-3-methoxy-crotonic acid diphenylmethyl ester, 6.7 ml of 1,2-dimethoxyethane and 0.22 ml of 1,5-diazabicyclo[5.4.0]undec-5-ene is stirred for 25 minutes at room temperature under a nitrogen atmosphere. The reaction mixture is diluted with toluene, washed successively with 2 N hydrochloric acid, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated by evaporation in vacuo. The residue, after preparative thick layer chromatography on silica gel using toluene/ethyl acetate, 1:1, gives 7β-phenylacetamido-3-methoxy-ceph-2-em-4α-carboxylic acid diphenylmethyl ester of melting point 166-169° C. (from methylene chloride/hexane), UV spectrum (ethanol): λmax = 258 mμ (ε = 4,500) IR spectrum (methylene chloride): characteristic bands at 2.93, 5.62, 5.73, 5.93 and 6.66 μ, Rf value~0.54 (silica gel; system toluene/ethyl acetate, 1:1), and amorphous 7β-phenylacetamido-3-methoxy-ceph-3-em-4-carboxylic acid diphenylmethyl ester, UV spectrum (ethanol): λmax =258 mμ (ε = 6,350), 264 mμ (ε = 6,350), 282 mμ (ε = 5,600) (shoulder), IR spectrum (methylene chloride): characteristic bands at 2.94, 5.63, 5.83, 5.94, 6.26 and 6.66 μ, Rf value~0.37 (silica gel; system toluene/ethyl acetate, 1:1), in the ratio of 8:1.

Aufarbeitung

  1. washwashed successively with 2 N hydrochloric acid, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated by evaporation in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-851417f1d82441fea30c70feed1596f8
Quelldatensatz
uspto-grants-1979_04
Patentnummer
US04147864

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