6-Aminopenicillanic acid → HCID 12314047, 화합물

HRID 364727

반응식

HRID 364727 반응식
[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]

참가 물질

5

반응물 3

HCID 110826-Aminopenicillanic acidHCID 174291-PiperidinecarboxaldehydeHCID 81531Diisopropylethylamine

생성물 1

HCID 12314047HCID 12314047, 화합물수율 22,371.5%

시약·촉매·용매 1

HCID 6212Chloroform용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1880e61f9cc346b8afcdc0f324039003
출처 데이터셋
uspto-grants-1986_08
특허 번호
US04605744

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