Ampicillin → 6-[(Aminophenylacetyl) amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid z,z,z-octadeca-6,9,12-trienamide

HRID 28308

Reaktionsgleichung

Reaktionsgleichung von HRID 28308
C([N:3](CC)CC)C.[CH3:8][C:9]1([CH3:31])[S:13][C@@H:12]2[C@H:14]([NH:17][C:18]([C@H:20]([NH2:27])[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[O:19])[C:15](=[O:16])[N:11]2[C@H:10]1[C:28]([OH:30])=[O:29].[C:32]([OH:51])(=O)[CH2:33][CH2:34][CH2:35][CH2:36]/[CH:37]=[CH:38]\[CH2:39]/[CH:40]=[CH:41]\[CH2:42]/[CH:43]=[CH:44]\[CH2:45][CH2:46][CH2:47][CH2:48][CH3:49].C1COCC1.CCCCCC>CN(C=O)C.CCCCCC.O>[NH2:27][CH:20]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:18]([NH:17][CH:14]1[C:15](=[O:16])[N:11]2[CH:12]1[S:13][C:9]([CH3:31])([CH3:8])[CH:10]2[C:28]([OH:30])=[O:29])=[O:19].[C:32]([NH2:3])(=[O:51])[CH2:33][CH2:34][CH2:35][CH2:36]/[CH:37]=[CH:38]\[CH2:39]/[CH:40]=[CH:41]\[CH2:42]/[CH:43]=[CH:44]\[CH2:45][CH2:46][CH2:47][CH2:48][CH3:49]

Komponenten

8

Edukt 4

HCID 6249AmpicillinHCID 8471TriethylamineHCID 5280933Gamma-Linolenic acidHCID 21883165Tetrahydrofuran hexane

Produkt 1

HCID 691995086-[(Aminophenylacetyl) amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid z,z,z-octadeca-6,9,12-trienamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

Triethylamine (0.3 ml) was added to a stirred suspension of ampicillin (0.7 g) in anhydrous DMF (120 ml) under a nitrogen atmosphere. To the resultant clear solution was added z,z,z-octadeca-6,9,12-trienoic acid, N-hydroxysuccinimide ester (0.75 g) while maintaining the reaction at 0-10° C. The reaction was stirred at this temperature for an additional hour before allowing the mixture to stand at room temperature overnight. Tlc analysis (40% THF/hexane) at this point indicated that most of the succinimide ester had reacted. Water (40 ml) was added to the reaction flask and the contents stirred. The solution was then neutralised and extracted with ethyl acetate. The extract was washed with water, dried (sodium sulfate) and concentrated to dryness leaving the crude product as a yellow glass. Trituration with hexane yielded 6-[(aminophenylacetyl) amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid-z,z,z-octadeca-6,9,12-trienamide as a yellow powder.

Aufarbeitung

  1. temperaturewhile maintaining
  2. customthe reaction at 0-10° C
  3. customhad reacted
  4. stirringthe contents stirred
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialdried (sodium sulfate)
  8. concentrationconcentrated to dryness
  9. customleaving the crude product as a yellow glass

Quellen und Nachweise

ORD-Eintrag
ord-01e0b3a578a34c49bce262894dec7794
Quelldatensatz
uspto-grants-2008_09
Patentnummer
USRE040480E1

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