Triethylamine → 6-(3-[Carbamoyl]-acrylamido)-2,2-dimethyl-3-(5-tetrazolyl)penam

HRID 614143

反応式

HRID 614143 の反応式
[C:1]([OH:8])(=O)/[CH:2]=[CH:3]\[C:4]([NH2:6])=[O:5].C(N(CC)CC)C.ClC(OCC(C)C)=O.[NH2:24][CH:25]1[C:38](=[O:39])[N:27]2[CH:28]([C:33]3[NH:37][N:36]=[N:35][N:34]=3)[C:29]([CH3:32])([CH3:31])[S:30][C@H:26]12>CN1CCOCC1.O1CCCC1.O>[C:4]([CH:3]=[CH:2][C:1]([NH:24][CH:25]1[C:38](=[O:39])[N:27]2[CH:28]([C:33]3[NH:34][N:35]=[N:36][N:37]=3)[C:29]([CH3:31])([CH3:32])[S:30][C@H:26]12)=[O:8])(=[O:5])[NH2:6]

参加物

8

反応物 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 5280451Maleamic acidHCID 178431949HCID 178431949、化合物

生成物 1

HCID 1784319306-(3-[Carbamoyl]-acrylamido)-2,2-dimethyl-3-(5-tetrazolyl)penam収率 33%

試薬・触媒・溶媒 3

HCID 79724-Methylmorpholine触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a stirred mixture of 1.15 g. (10 m mole) of maleamic acid and 1.40 ml. of triethylamine in 40 ml. of dry tetrahydrofuran, at 0° C., is added 1.57 ml. (12 m mole) of isobutyl chloroformate followed by three drops of N-methylmorpholine. Stirring is continued for a further 30 minutes at 0° C. To this mixed anhydride is then added a solution prepared by adding 2.40 g. (10 m mole) of 6-amino-2,2-dimethyl-3-(5-tetrazolyl)penam to a mixture of 15 ml. of water and 15 ml. of tetrahydrofuran and adjusting the pH to 7.5. The resulting mixture is then stirred for a further 1 hour at 0° C. At this point, the tetrahydrofuran is removed by evaporation in vacuo, and the residue is diluted with more water. The pH is adjusted to 8.0 with 6 N sodium hydroxide, and then the mixture is extracted with ethyl acetate. The extracts are discarded. The pH of the residual aqueous phase is adjusted to 2.0 with 4 N hydrochloric acid and then the product is extracted into ethyl acetate. The organic layer is dried and concentrated in vacuo to give 6-(3-[carbamoyl]-acrylamido)-2,2-dimethyl-3-(5-tetrazolyl)penam (1.03 g., 33% yield). The infrared spectrum (KBr disc) of the product shows absorption bands at 1818 cm-1 (β-lactam) and 1692 cm-1. The NMR spectrum (DMSO-d6) shows bands at 7.00 and 6.25 (quartet, 2H, J = 12 Hz, olefinic hydrogens), 5.80-5.48 ppm (multiplet, 2H, C-5 and C-6 hydrogens), 5.26 ppm (singlet, 1H, C-3 hydrogen), 1.65 ppm (singlet, 3H, C-2 methyl hydrogens) and 1.06 ppm (singlet, 3H, C-2 methyl hydrogens).

後処理

  1. additionTo a stirred mixture of 1.15 g
  2. customprepared
  3. additionby adding 2.40 g
  4. stirringThe resulting mixture is then stirred for a further 1 hour at 0° C
  5. customAt this point, the tetrahydrofuran is removed by evaporation in vacuo
  6. additionthe residue is diluted with more water
  7. extractionthe mixture is extracted with ethyl acetate
  8. extractionthe product is extracted into ethyl acetate
  9. customThe organic layer is dried
  10. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-44e87e836fef40af80117f89a3231faf
出典データセット
uspto-grants-1979_03
特許番号
US04143039

関連ノート

読み込み中…