Potassium Carbonate → Cefuroxime Pivoxetil

HRID 745969

반응식

HRID 745969 반응식
[CH3:1][O:2]/[N:3]=[C:4](\[C:10]([NH:12][C@@H:13]1[C:16](=[O:17])[N:15]2[C:18]([C:27]([OH:29])=[O:28])=[C:19]([CH2:22][O:23][C:24]([NH2:26])=[O:25])[CH2:20][S:21][C@H:14]12)=[O:11])/[C:5]1[O:9][CH:8]=[CH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:37]([O:39][C:40](=[O:46])[C:41]([O:44][CH3:45])([CH3:43])[CH3:42])[CH3:38]>CN(C)C=O>[C:24]([O:23][CH2:22][C:19]1[CH2:20][S:21][C@@H:14]2[C@H:13]([NH:12][C:10](=[O:11])/[C:4](=[N:3]\[O:2][CH3:1])/[C:5]3[O:9][CH:8]=[CH:7][CH:6]=3)[C:16](=[O:17])[N:15]2[C:18]=1[C:27]([O:29][CH:37]([O:39][C:40](=[O:46])[C:41]([O:44][CH3:45])([CH3:43])[CH3:42])[CH3:38])=[O:28])(=[O:25])[NH2:26]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 5479529CefuroximeHCID 134780512-Methoxy-2-methylpropanoic acid 1-bromoethyl ester

생성물 1

HCID 6321417Cefuroxime Pivoxetil수율 38.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Cefuroxime (4.24 g) and powdered potassium carbonate (0.690 g) were stirred in anhydrous N,N-dimethylformamide (40 ml) till a solution was obtained. The solution was cooled to -3°, 2-methoxy-2-methylpropanoic acid 1-bromoethyl ester (2.50 g) was added and the solution was stirred for 1 hour. It was then partitioned between 2N hydrochloric acid (100 ml) and ethyl acetate (200 ml and 100 ml) and the combined organic layers were washed sequentially with 100 ml each of 2N hydrochloric acid (2×), water, saturated aqueous sodium bicarbonate, water (2×) and saturated brine, dried over magnesium sulphate and concentrated under reduced pressure to ca 20 ml. The solution was added slowly to petroleum ether (200 ml) and the resulting precipitate was filtered off, washed with petroleum ether and dried under vacuum to give the title ester (2.20 g); λmax (ethanol) 277.5 nm E11 342; νmax (CHBr3) 3520 and 3400 (NH and NH2), 1788 (β-lactam C=O), 1750 (ester C=O), 1732 (αβ unsaturated ester and carbamate C=O), and 1688 and 1514 cm-1 (amide C=O).

후처리

  1. customwas obtained
  2. temperatureThe solution was cooled to -3°
  3. customIt was then partitioned between 2N hydrochloric acid (100 ml) and ethyl acetate (200 ml and 100 ml)
  4. washthe combined organic layers were washed sequentially with 100 ml each of 2N hydrochloric acid (2×), water, saturated aqueous sodium bicarbonate, water (2×) and saturated brine
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated under reduced pressure to ca 20 ml
  7. additionThe solution was added slowly to petroleum ether (200 ml)
  8. filtrationthe resulting precipitate was filtered off
  9. washwashed with petroleum ether
  10. customdried under vacuum

출처 및 근거

ORD 기록
ord-2bbe109bba714ea8aa54b49a13060928
출처 데이터셋
uspto-grants-1986_07
특허 번호
US04602012

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