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Methanesulfonyl chloride → benzhydryl (6R,7R)-7-[[(2Z)-2-methoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-3-[(2-methyl-6-oxopyran-4-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 467379
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 467379
Cl.[C:2]([NH:21][C:22]1[S:23][CH:24]=[C:25](/[C:27](=[N:31]/[O:32][CH3:33])/[C:28](O)=[O:29])[N:26]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)C(C)C)(C)C.CS(Cl)(=O)=O.[NH2:48][C@@H:49]1[C:82](=[O:83])[N:51]2[C:52]([C:66]([O:68][CH:69]([C:76]3[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=3)[C:70]3[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=3)=[O:67])=[C:53]([CH2:56][S:57][C:58]3[CH:63]=[C:62]([CH3:64])[O:61][C:60](=[O:65])[CH:59]=3)[CH2:54][S:55][C@H:50]12>CN(C)C=O.N1C=CC=CC=1>[CH3:64][C:62]1[O:61][C:60](=[O:65])[CH:59]=[C:58]([S:57][CH2:56][C:53]2[CH2:54][S:55][C@@H:50]3[C@H:49]([NH:48][C:28](=[O:29])/[C:27](/[C:25]4[N:26]=[C:22]([NH:21][C:2]([C:3]5[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=5)([C:15]5[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=5)[C:9]5[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=5)[S:23][CH:24]=4)=[N:31]\[O:32][CH3:33])[C:82](=[O:83])[N:51]3[C:52]=2[C:66]([O:68][CH:69]([C:70]2[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=2)[C:76]2[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=2)=[O:67])[CH:63]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 95660662-(Tritylamino)-alpha-(methoxyimino)-4-thiazoleacetic acid, predominantly syn hydrochlorideHCID 67908188Diphenylmethyl 7beta-Amino-3-(6-methyl-2-oxo-2H-pyran-4-ylthiomethyl)ceph-3-em-4-carboxylate

Produkt 1

HCID 88501676
benzhydryl (6R,7R)-7-[[(2Z)-2-methoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-3-[(2-methyl-6-oxopyran-4-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
Ausbeute 70,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A stirred solution of 2-(2-tritylaminothiazol-4-yl)-2-(Z)-methoxyiminoacetic acid hydrochloride (470 mg) and N,N-diisopropylethylamine (0.34 ml) in dimethylformamide (4 ml) was cooled to -55° to -60° C. and methanesulphonyl chloride (0.075 ml) was added. The mixture was stirred at the same temperature for 0.5 h and then a solution of diphenymethyl 7β-amino-3-(6-methyl-2-oxo-2H-pyran-4-ylthiomethyl)ceph-3-em-4-carboxylate (450 mg) in dimethylformamide (4 ml) was added, followed by pyridine (0.071 ml). The mixture was stirred at 0° C. for 1.5 h and then partitioned between ethyl acetate and citric acid solution. The organic phase was then washed successively with water, sodium bicarbonate solution, water and brine. The solution was dried over magnesium sulphate and evaporated. The product (576 mg) was isolated by column chromatography of the residue using gradient elution (Kieselgel 1:1 hexane:ethyl acetate going to neat ethyl acetate). υmax (CHCl3) 3400, 1780, 1710 and 1680(s). δ(CDCl3) 2.18 (3H, s), 3.46 (1H, d, J 18.3Hz), 3.61 (1H, d, J 18.4Hz), 3.85 (1H, d, J 12.3Hz), 3.96 (1H, d, J 12.3Hz), 4.08 (3H, s), 5.08 (1H, d, J 4.9Hz), 5.69 (1H, s), 5.78 (1H, s), 5.96 (1H, dd, J 4.9 and 8.9Hz), 6.74 (1H, s), 6.81 (1H, d, J 8.8Hz), 6.97 (1H, s), 7.02 (1H, s), 7.2-7.5 (25H, m). [Mass spectrum: +ve ion (3NOBA, Na+) MNa+ 1196].

Aufarbeitung

  1. stirringThe mixture was stirred at 0° C. for 1.5 h
  2. custompartitioned between ethyl acetate and citric acid solution
  3. washThe organic phase was then washed successively with water, sodium bicarbonate solution, water and brine
  4. dry with materialThe solution was dried over magnesium sulphate
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-6320acf1148b48fb99fc4dcf3c85cc60
Quelldatensatz
uspto-grants-1992_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05158946

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