Pyridine → HCID 178423843, Verbindung

HRID 973870Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 973870
[C:1]1([C:7]([NH:20][C:21]2[S:22][CH:23]=[C:24](/[C:26](=[N:30]/[O:31][C:32]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)/[C:27]([O-:29])=O)[N:25]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[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.[Na+].CS(Cl)(=O)=O.[NH2:57][C@@H:58]1[C:89](=[O:90])[N:60]2[C:61]([C:73]([O:75][CH:76]([C:83]3[CH:88]=[CH:87][CH:86]=[CH:85][CH:84]=3)[C:77]3[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=3)=[O:74])=[C:62](/[CH:65]=[C:66]3\[CH:67]=[C:68]([CH3:72])[C:69](=[O:71])[O:70]\3)[CH2:63][S:64][C@H:59]12.N1C=CC=CC=1>CN(C=O)C.C(OCC)(=O)C>[CH3:72][C:68]1[C:69](=[O:71])[O:70]/[C:66](=[CH:65]/[C:62]2[CH2:63][S:64][C@@H:59]3[C@H:58]([NH:57][C:27](=[O:29])/[C:26](=[N:30]\[O:31][C:32]([C:45]4[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=4)([C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)/[C:24]4[N:25]=[C:21]([NH:20][C:7]([C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)([C:8]5[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=5)[C:14]5[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=5)[S:22][CH:23]=4)[C:89](=[O:90])[N:60]3[C:61]=2[C:73]([O:75][CH:76]([C:77]2[CH:78]=[CH:79][CH:80]=[CH:81][CH:82]=2)[C:83]2[CH:88]=[CH:87][CH:86]=[CH:85][CH:84]=2)=[O:74])/[CH:67]=1

Komponenten

7

Edukt 4

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 23714200sodium (2Z)-2-[2-(tritylamino)-1,3-thiazol-4-yl]-2-trityloxyiminoacetateHCID 67923953diphenylmethyl 7beta-amino-3-(E-2,5-dihydro-3-methyl-2-oxofuran-5-ylidenemethyl)ceph-3-em-4-carboxylate

Produkt 1

HCID 178423843HCID 178423843, VerbindungAusbeute 39,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

Sodium 2-(2-triphenylmethylaminothiazol-4-yl)2-Z-triphenylmethoxyiminoacetate (0.832 g), in dry DMF (2 mls) was cooled to ca -50° C. under argon and treated with methanesulphonyl chloride (0.093 mls). The solution was allowed to warm to -15° C. over 30mins and then treated with a solution of diphenylmethyl 7β-amino-3-(E-2,5-dihydro-3-methyl-2-oxofuran-5-ylidenemethyl)ceph-3-em-4-carboxylate (0.474 g) and pyridine (0.096 mls) in DMF (3 mls). The reaction was allowed to warm to room temperature over 1h., diluted with ethyl acetate and washed with water (3×), brine and dried. After removal of solvent, flash chromatography on silica gel eluting with 30, 40% ethyl acetate/hexane, gave the title compound as a foam, (0.444 g, 39%), νmax (CH2Cl2) 3375, 1780 (shoulder), 1760, 1720, 1680 and 1500cm-1 ; δH (CDCl3) 1.88 (3H,s), 3.37 (2H,ABq, J17.6Hz), 5.14 (1H,d,J5.1Hz), 6.10 (1H,dd,J5.1,8.8Hz), 6.44 (1H,s), 6.48 (1H,s) 6.77 (1H,br.s, exch.), 6.98 (1H,s), 7.00 (1H,s) and 7.2-7.4 (40H,m); [mass spectrum: +ve ion (NOBA) MH+, 1128].

Aufarbeitung

  1. temperatureto warm to room temperature over 1h.
  2. washwashed with water (3×), brine
  3. customdried
  4. customAfter removal of solvent, flash chromatography on silica gel eluting with 30, 40% ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-d048aa5349164c9aa466d6dfeb8ca40b
Quelldatensatz
uspto-grants-1991_11
Patentnummer
US05064649

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