4-(Bromomethyl)-5-methyl-1,3-dioxol-2-one → (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl (6R)-7-[[(2Z)-2-methoxyimino-2-(1,3-thiazol-4-yl)acetyl]amino]-8-oxo-3-(1,2,4-thiadiazol-5-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 34267Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 34267
Br[CH2:2][C:3]1[O:4][C:5](=[O:9])[O:6][C:7]=1[CH3:8].[CH3:10][O:11]/[N:12]=[C:13](/[C:36]1[N:37]=[CH:38][S:39][CH:40]=1)\[C:14]([NH:16][CH:17]1[C:34](=[O:35])[N:19]2[C:20]([C:31]([O-:33])=[O:32])=[C:21]([CH2:24][S:25][C:26]3[S:30][N:29]=[CH:28][N:27]=3)[CH2:22][S:23][C@H:18]12)=[O:15].[Na+]>CN(C)C=O>[CH3:8][C:7]1[O:6][C:5](=[O:9])[O:4][C:3]=1[CH2:2][O:33][C:31]([C:20]1[N:19]2[C:34](=[O:35])[CH:17]([NH:16][C:14](=[O:15])/[C:13](=[N:12]\[O:11][CH3:10])/[C:36]3[N:37]=[CH:38][S:39][CH:40]=3)[C@H:18]2[S:23][CH2:22][C:21]=1[CH2:24][S:25][C:26]1[S:30][N:29]=[CH:28][N:27]=1)=[O:32]

Komponenten

4

Edukt 2

HCID 107741414-(Bromomethyl)-5-methyl-1,3-dioxol-2-oneHCID 88640700sodium (6R)-7-[[(2Z)-2-methoxyimino-2-(1,3-thiazol-4-yl)acetyl]amino]-8-oxo-3-(1,2,4-thiadiazol-5-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Produkt 1

HCID 172930572(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl (6R)-7-[[(2Z)-2-methoxyimino-2-(1,3-thiazol-4-yl)acetyl]amino]-8-oxo-3-(1,2,4-thiadiazol-5-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-Bromomethyl-5-methyl-1,3-dioxolene-2-one (386 mg) was added to a solution of sodium 7-[(Z)-2-methoxyimino-2-(thiazol-4-yl)acetamido]-3-(1,2,4-thiadiazol-5-yl)thiomethyl-3-cephem-4-carboxylate (522 mg) in N,N-dimethylformamide (5 ml) at -5° C. and the mixture was stirred at this temperature for 1.3 hr. The reaction mixture was then treated in the same manner as in Example 14, giving the title compound (190 mg). ##STR39##

Aufarbeitung

  1. additionThe reaction mixture was then treated in the same manner as in Example 14

Quellen und Nachweise

ORD-Eintrag
ord-e9ce1ee0f8444199b4d7994e2d1adb06
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04761409

Notizen zur Reaktion

Wird geladen…