反応 #56586

反応方程式

Triethylamine

ampicillin

z,z,z-octadeca-6,9,12-trienoic acid

THF hexane

→

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

溶媒

hexane

DMF

Water

反応条件

後処理

1. 1
   温度while maintaining
2. 2
   その他the reaction at 0-10° C
3. 3
   その他had reacted
4. 4
   workup.STIRRINGthe contents stirred
5. 5
   抽出extracted with ethyl acetate
6. 6
   洗浄The extract was washed with water
7. 7
   乾燥dried (sodium sulfate)
8. 8
   濃縮concentrated to dryness
9. 9
   その他leaving the crude product as a yellow glass

実験手順

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.

出典