benzhydryl (6R,7R)-7-[[(2Z)-2-(2-amino-5-chloro-1,3-thiazol-4-yl)-2-trityloxyiminoacetyl]amino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate → benzhydryl (6R,7R)-7-[[(2Z)-2-(2-amino-5-chloro-1,3-thiazol-4-yl)-2-trityloxyiminoacetyl]amino]-8-oxo-3-sulfanyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 342938Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 342938
[C:1]1([CH:7]([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:57])[C@@H:24]([NH:25][C:26](=[O:56])/[C:27](/[C:49]4[N:50]=[C:51]([NH2:55])[S:52][C:53]=4[Cl:54])=[N:28]\[O:29][C:30]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)C4C=CC=CC=4)[C@H:21]3[S:20][CH2:19][C:18]=2Cl)=[O:16])C2C=CC=CC=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[SH2:60].[Na].P(O)(O)([O-])=O.[Na+]>CN(C=O)C>[C:1]1([CH:7]([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:57])[C@@H:24]([NH:25][C:26](=[O:56])/[C:27](/[C:49]4[N:50]=[C:51]([NH2:55])[S:52][C:53]=4[Cl:54])=[N:28]\[O:29][C:30]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)([C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)[C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[C@H:21]3[S:20][CH2:19][C:18]=2[SH:60])=[O:16])[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 10581389benzhydryl (6R,7R)-7-[[(2Z)-2-(2-amino-5-chloro-1,3-thiazol-4-yl)-2-trityloxyiminoacetyl]amino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateHCID 23672064Monosodium phosphateHCID 53442613Sodium hydrogen sulfide hydrate

Produkt 1

HCID 141584533benzhydryl (6R,7R)-7-[[(2Z)-2-(2-amino-5-chloro-1,3-thiazol-4-yl)-2-trityloxyiminoacetyl]amino]-8-oxo-3-sulfanyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateAusbeute 190,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of (7R)-7-[(Z)-2-(2-amino-5-chlorothiazol-4-yl)-2-(triphenylmethoxyimino)acetamido]-3-chloro-3-cephem-4-carboxylate diphenylmethyl ester (4.0 g , 4.72 mmol) in DMF (30 mL) cooled to -20° C. was added in one portion powdered sodium hydrogen sulfide hydrate (1.1 g, 19.6 mmol). After 15 min the reaction mixture was poured into 0.5M monosodium phosphate (about 100 mL), extracted with ethyl acetate and the organic layer was washed thoroughly with water. After concentrating in vacuum the crude title product was obtained as yellow foam 3.8 g (95%). 1H NMR (CDCl3 /CD3OD) δ 3.38 (d, 1H, J=15), 4.43 (d, 1H, J=15), 5.03 (d, 1H, J=5), 5.80 (d, 1H, J=5), 5.99 (br s, 1H), 6.80 (s, 1H), 7.05-7.50 (m, 25H).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washthe organic layer was washed thoroughly with water
  3. concentrationAfter concentrating in vacuum the crude title product

Quellen und Nachweise

ORD-Eintrag
ord-0c4182de80b84d36b8af14a4a12f79d3
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05859256

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