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Water → 7beta-Phenoxyacetamido-3-hydroxy-3-cephem-4-carboxylic acid p-nitrobenzyl ester

HRID 1388954
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1388954
[N+:1]([C:4]1[CH:48]=[CH:47][C:7]([CH2:8][O:9][C:10](=[O:46])/[C:11](/[N:19]2[CH:22]([S:23]S(C3C=CC(C)=CC=3)(=O)=O)[CH:21]([NH:34][C:35](=[O:44])[CH2:36][O:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[C:20]2=[O:45])=[C:12](\N2CCCC2)/[CH3:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].C1(C)C=CC=CC=1.C(OCC)(=[O:58])C.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C(#N)C.C1C=CC=CC=1>[N+:1]([C:4]1[CH:48]=[CH:47][C:7]([CH2:8][O:9][C:10]([C:11]2[N:19]3[C:20](=[O:45])[C@@H:21]([NH:34][C:35](=[O:44])[CH2:36][O:37][C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)[C@H:22]3[S:23][CH2:13][C:12]=2[OH:58])=[O:46])=[CH:6][CH:5]=1)([O-:3])=[O:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 12784133HCID 12784133, VerbindungHCID 21584019Toluene ethylacetate

Produkt 1

HCID 547167947beta-Phenoxyacetamido-3-hydroxy-3-cephem-4-carboxylic acid p-nitrobenzyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241
Benzene
Lösungsmittel
HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of 160 mg (0.23 mmol) of a mixture consisting of 2-[4-(p-toluenesulphonylthio)-3-phenoxyacetamido-2-oxoazetidin-1-yl]-3-(1-pyrrolidyl)-crotonic acid p-nitrobenzyl ester and the corresponding isocrotonic acid ester in 3 ml of dry acetonitrile is heated under nitrogen for about 4 hours at 80° C. until no further starting material can be detected by thin layer chromatography (silica gel; toluene/ethyl acetate, 1:1). The heating bath is removed, p-toluenesulphonic acid (about 0.23 mmol) and 0.2 ml of water are added to the reaction mixture containing the 7β-phenoxyacetamido-3-pyrrolidino-cephem-4-carboxylic acid p-nitrobenzyl ester and the mixture is stirred for a further 2 hours at room temperature. The reaction mixture is diluted with benzene, washed with water, dried over sodium sulphate and evaporated in vacuo. The residue is triturated at 0° C. with diethyl ether and gives the pale yellow 7β-phenoxyacetamido-3-hydroxy-3-cephem-4-carboxylic acid p-nitrobenzyl ester. IR spectrum (methylene chloride): characteristic bands at 2.95; 3.3; 5.6; 5.75 (sh); 5.9; 5.95 (sh); 6.55; 7.45; 8.15 and 8.3μ; NMR spectrum (deuterochloroform): δ in ppm: 3.4 (2H, 2, J= 17 Hz); 4.57 (2H, s); 5.06 (1H, d; J=5 Hz); 5.35 (2H, q, J=14 Hz); 5.7 (1H, dd, J=5.10 Hz); 6.8-8.4 (10H, c) and 11.4 (1H, br.s.).

Aufarbeitung

  1. customThe heating bath is removed
  2. washwashed with water
  3. dry with materialdried over sodium sulphate
  4. customevaporated in vacuo
  5. customThe residue is triturated at 0° C. with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-379c0b0dce12413a8fe9db21acc0e775
Quelldatensatz
uspto-grants-1984_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04434287

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