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Acetic Anhydride → 4-nitrobenzyl(5R)-6-[(acetyloxy)([1,3]thiazolo[3,2-a]benzimidazol-6-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

HRID 638900
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 638900
[S:1]1[CH:5]=[CH:4][N:3]2[C:6]3[CH:12]=[C:11]([CH:13]=[O:14])[CH:10]=[CH:9][C:7]=3[N:8]=[C:2]12.[Br-].[Mg+2].[Br-].[N+:18]([C:21]1[CH:39]=[CH:38][C:24]([CH2:25][O:26][C:27]([C:29]2[N:30]3[CH:33]([S:34][CH:35]=2)[CH:32]([Br:36])[C:31]3=[O:37])=[O:28])=[CH:23][CH:22]=1)([O-:20])=[O:19].[C:40](OC(=O)C)(=[O:42])[CH3:41]>C(OCC)(=O)C.C(N(CC)CC)C.C1COCC1.C(#N)C>[C:40]([O:14][CH:13]([C:11]1[CH:10]=[CH:9][C:7]2[N:8]=[C:2]3[S:1][CH:5]=[CH:4][N:3]3[C:6]=2[CH:12]=1)[C:32]1([Br:36])[C:31](=[O:37])[N:30]2[C@@H:33]1[S:34][CH:35]=[C:29]2[C:27]([O:26][CH2:25][C:24]1[CH:38]=[CH:39][C:21]([N+:18]([O-:20])=[O:19])=[CH:22][CH:23]=1)=[O:28])(=[O:42])[CH3:41]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 7918Acetic AnhydrideHCID 82241Magnesium BromideHCID 22224493Benzo[4,5]imidazo[2,1-b]thiazole-6-carbaldehydeHCID 684433356-Bromo-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Produkt 1

HCID 69608597
4-nitrobenzyl(5R)-6-[(acetyloxy)([1,3]thiazolo[3,2-a]benzimidazol-6-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
Ausbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6342AcetonitrileLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

A 30 ml acetonitrile solution of benzo[4,5]imidazo[2,1-b]thiazole-6-carbaldehyde (404 mg, 2 mmol) was added 1.03 gram of magnesium bromide etherate. The mixture was stirred at 23° C. for half an hour. Then a 30 ml dry THF solution of the 6-Bromo-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (770 mg, 2 mmol) was injected within a minute and the reaction mixture was then cooled to −20° C. Triethylamine (0.7 ml, eq.) was then injected and the reaction mixture was stirred for five hours at −20° C. Then acetic anhydride (0.377 ml, eq.) was injected and the reaction mixture was left at zero degree for 18 hours. The reaction media was then diluted with 400 ml ethyl acetate and washed with 100 ml 5% citric acid, 100 ml saturated sodium bicarbonate, and 100 ml brine. The organic layer was then dried over magnesium sulfate, filtered and concentrated. Flash column chromatography using 20% ethyl acetate in hexane gave 630 mg product. (50% Yield); MS: 631.9 (M+H)

Aufarbeitung

  1. temperaturethe reaction mixture was then cooled to −20° C
  2. stirringthe reaction mixture was stirred for five hours at −20° C
  3. customThe reaction media
  4. washwashed with 100 ml 5% citric acid, 100 ml saturated sodium bicarbonate, and 100 ml brine
  5. dry with materialThe organic layer was then dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-1b7a495c2419485aab007e23b6b86772
Quelldatensatz
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07691842B2

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