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 2380736

Reaction equation

HRID 2380736 reaction equation
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]

Participants

8

Reactant 4

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

Product 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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-7de0227dfca043fd8a65a6ef5c2c8a90
Source dataset
uspto-grants-2012_09
Patent number
USRE043632E1

Linked notes

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