Water → (2-methoxy-2-methylpropanoyl)oxymethyl (6R,7R)-3-(carbamoyloxymethyl)-7-[[(2Z)-2-(furan-2-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 745968

반응식

HRID 745968 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+].I[CH2:37][O:38][C:39](=[O:45])[C:40]([O:43][CH3:44])([CH3:42])[CH3:41].O>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](/[C:5]3[O:9][CH:8]=[CH:7][CH:6]=3)=[N:3]\[O:2][CH3:1])[C:16](=[O:17])[N:15]2[C:18]=1[C:27]([O:29][CH2:37][O:38][C:39](=[O:45])[C:40]([O:43][CH3:44])([CH3:42])[CH3:41])=[O:28])(=[O:25])[NH2:26]

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 5479529CefuroximeHCID 22145393Iodomethyl 2-methoxy-2-methylpropanoate

생성물 1

HCID 13478066(2-methoxy-2-methylpropanoyl)oxymethyl (6R,7R)-3-(carbamoyloxymethyl)-7-[[(2Z)-2-(furan-2-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate수율 69.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

Cefuroxime (1.697 g) and powdered potassium carbonate (276 mg) were stirred in anhydrous N,N-dimethylformamide (20 ml) at 22° for 1 hour and the resulting solution was cooled in an ice/salt bath to -8°. A solution of crude 2-methoxy-2-methylpropanoic acid iodomethyl ester (1.52 g) in anhydrous N,N-dimethylformamide (6 ml) was added and the solution was stirred for 35 mins. Water (75 ml) was added and the mixture was extracted with ethyl acetate (2×100 ml). The combined organic layers were washed successively with 50 ml each of 2N hydrochloric acid (3×), water, saturated aqueous sodium bicarbonate, water, 10% aqueous sodium metabisulphite, water (2×) and saturated brine, dried over magnesium sulphate and concentrated under vacuum to ca 10 ml. The solution was added dropwise to stirred petroleum ether (100 ml) to give a precipitate which was filtered off, washed with petroleum ether and dried under reduced pressure to give the title ester (1.532 g); λmax (ethanol 277) nm E11 323; νmax (CHBr3) 3520 and 3400 (NH and NH2), 1788 (β-lactam C=O); 1735 (ester and carbamate C=O) and 1685 and 1510 cm-1 (amide C=O).

후처리

  1. temperaturethe resulting solution was cooled in an ice/salt bath to -8°
  2. extractionthe mixture was extracted with ethyl acetate (2×100 ml)
  3. washThe combined organic layers were washed successively with 50 ml each of 2N hydrochloric acid (3×), water, saturated aqueous sodium bicarbonate, water, 10% aqueous sodium metabisulphite, water (2×) and saturated brine
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated under vacuum to ca 10 ml
  6. additionThe solution was added dropwise
  7. stirringto stirred petroleum ether (100 ml)
  8. customto give a precipitate which
  9. filtrationwas filtered off
  10. washwashed with petroleum ether
  11. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-58a710ae07af42bb9c02a77b1ef85639
출처 데이터셋
uspto-grants-1986_07
특허 번호
US04602012

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