6-Aminopenicillanic acid → HCID 12314047、化合物

HRID 364727

反応式

HRID 364727 の反応式
[CH3:1][C:2]1([CH3:14])[S:6][C@@H:5]2[C@H:7](N)[C:8](=[O:9])[N:4]2[C@H:3]1[C:11]([OH:13])=[O:12].C(N(C(C)C)CC)(C)C.N1(C=O)CCCCC1>C(Cl)(Cl)Cl>[CH3:1][C:2]1([CH3:14])[S:6][CH:5]2[N:4]([C:8](=[O:9])[CH2:7]2)[CH:3]1[C:11]([OH:13])=[O:12]

参加物

5

反応物 3

HCID 110826-Aminopenicillanic acidHCID 174291-PiperidinecarboxaldehydeHCID 81531Diisopropylethylamine

生成物 1

HCID 12314047HCID 12314047、化合物収率 22,371.5%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒2 回

実験手順

A mixture of 4-[3-(1H-imidazol-1-yl)propyl]-piperidine (1.5 g, 0.0078M) and dimethylformamide dimethylacetal (10 ml) was heated at 100° C. for 16 hrs. The excess of dimethylformamide dimethylacetal was removed to give 4-[3-(1H-imidazol-1-yl)propyl]-1-piperidinecarboxaldehyde dimethylacetal. To the mixture of 6-aminopenicillanic acid (1.16 g, 0.0053M) and diisopropylethylamine (1.03 ml) in dry CHCl3 (9 ml) was added the above piperidinecarboxaldehyde in CHCl3 (5 ml) at 0° C. and stirred at that temperature for 1 hr, then at room temperature for 3 hrs. After the reaction, the solvent was removed and the residue dissolved in water (40 ml). The aqueous solution, washed with diethyl ether, was adjusted to pH 3 with dilute aqueous HCl and purified on Sephadex LH 20 column to give [2S-(2alpha,5alpha,6beta)]-6-[[4-[3-(1 H-imidazol-1-yl)propyl]-1-piperidinyl]methylene]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 1.2 mole hydrochloride monohydrate (0.87 g, 39% yield).

後処理

  1. waitat room temperature for 3 hrs
  2. customAfter the reaction
  3. customthe solvent was removed
  4. dissolutionthe residue dissolved in water (40 ml)
  5. washThe aqueous solution, washed with diethyl ether
  6. custompurified on Sephadex LH 20 column

出典と根拠

ORDレコード
ord-1880e61f9cc346b8afcdc0f324039003
出典データセット
uspto-grants-1986_08
特許番号
US04605744

関連ノート

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