Dimethylformamide dimethyl acetal → HCID 13281184, 화합물

HRID 364705노트

반응식

HRID 364705 반응식
[N:1]1([CH2:6][CH2:7][CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:5]=[CH:4][N:3]=[CH:2]1.[CH3:14][O:15][CH:16]([O:20][CH3:21])N(C)C>>[CH3:14][O:15][CH:16]([O:20][CH3:21])[N:11]1[CH2:12][CH2:13][CH:8]([CH2:7][CH2:6][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)[CH2:9][CH2:10]1

참가 물질

3

반응물 2

HCID 78373Dimethylformamide dimethyl acetalHCID 132811834-[2-(1H-imidazol-1-yl)ethyl]piperidine

생성물 1

HCID 13281184HCID 13281184, 화합물수율 87%

실험 절차

The free base 4[2-(imidazol-1-yl)ethyl]piperidine (5.1 g, 28.7 mM) and dimethylformamide dimethyl acetal (23 ml) was heated at 100° C. for 6 hours. Removal of the excess of dimethylformamide dimethyl acetal gave 4-[2-(imidazol-1-yl)ethyl]-1-piperidine carboxaldehyde dimethylacetal (6.32 g, 87%) which was dissolved in CH2Cl2 (27 ml) and added to the mixture of 6-aminopenicillanic acid (5.6 g, 258 mM) and diisopropylethylamine (3.41 ml) in CH2Cl2 (100 ml) at 0° C. The reaction was stirred at 0° C. for 1 hr. and room temperature for 3 hrs. The solvent was then removed and water (100 ml) was added. After being washed with ethylacetate, the aqueous solution, acidified to pH 3, was purified on Sephadex LH 20 columns to give [2S-(2alpha,5alpha,6beta)]-6-[[[4 -[2-(1H-imidazol-1-yl)ethyl]-1-piperidinyl]methylene]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid hydrate hydrochloride (1.8 g, 16% yield).

후처리

  1. customRemoval of the excess of dimethylformamide dimethyl acetal

출처 및 근거

ORD 기록
ord-0cc13518dc3b4097aef05c6c2825eb96
출처 데이터셋
uspto-grants-1986_08
특허 번호
US04605744

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