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 2116422

反応式

HRID 2116422 の反応式
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]

参加物

8

反応物 4

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

生成物 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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8058Hexane溶媒

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.

後処理

  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

出典と根拠

ORDレコード
ord-561a2a3c2fdb44228975b64b8cd17961
出典データセット
uspto-grants-2008_10
特許番号
USRE040546E1

関連ノート

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