Phosphorisocyanatidic dichloride → Cefuroxime

HRID 894834

반응식

HRID 894834 반응식
ClP([N:5]=[C:6]=[O:7])(Cl)=O.[O:8]1[CH:12]=[CH:11][CH:10]=[C:9]1/[C:13](=[N:31]/[O:32][CH3:33])/[C:14]([NH:16][C@@H:17]1[C:29](=[O:30])[N:19]2[C:20]([C:26]([OH:28])=[O:27])=[C:21]([CH2:24][OH:25])[CH2:22][S:23][C@H:18]12)=[O:15].C([O-])(=O)C.[Na+]>C1COCC1.O>[CH3:33][O:32]/[N:31]=[C:13](\[C:14]([NH:16][C@@H:17]1[C:29](=[O:30])[N:19]2[C:20]([C:26]([OH:28])=[O:27])=[C:21]([CH2:24][O:25][C:6]([NH2:5])=[O:7])[CH2:22][S:23][C@H:18]12)=[O:15])/[C:9]1[O:8][CH:12]=[CH:11][CH:10]=1

참가 물질

6

반응물 3

HCID 70090Phosphorisocyanatidic dichlorideHCID 517045Sodium Acetate2회HCID 9800056(6R,7R)-7-(((2Z)-2-(2-Furanyl)-2-(methoxyimino)acetyl)amino)-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid

생성물 1

HCID 5479529Cefuroxime

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Dichlorophosphinyl isocyanate (1.46 ml,) was added to a solution of (6R,7R)-7-[Z-2-(fur-2-yl)-2-methoxyiminoacetamido]-3-hydroxymethylceph-3-em-4-carboxylic acid (3.81 g) in THF (50 ml) at 22°, the temperature rising to 31°. The reaction mixture was stirred for 15 minutes and then added to a solution of sodium acetate (5.72 g) in water (50 ml). More sodium acetate (1.64 g) was added over 10 minutes to give a stable pH of 4.6. This solution was stirred at 30° for 1 hour and then heated at 45° for 3.5 hours when TLC (as Example 3) showed the reaction to be complete. The solution, pH 4.6, was clarified by filtration, adjusted to pH 7.0 with aqueous NaHCO3 solution and washed twice with ethyl acetate. The aqueous phase was stirred and acidified to pH 1.9 with dilute hydrochloric acid to precipitate the title compound (2.80 g, 66.0%); purity by HPLC 95.8% and by TLC 96%.

후처리

  1. customrising to 31°
  2. customto give a stable pH of 4.6
  3. stirringThis solution was stirred at 30° for 1 hour
  4. temperatureheated at 45° for 3.5 hours when TLC (as Example 3)
  5. customthe reaction
  6. filtrationThe solution, pH 4.6, was clarified by filtration
  7. washwashed twice with ethyl acetate
  8. stirringThe aqueous phase was stirred
  9. customto precipitate the title compound (2.80 g, 66.0%)

출처 및 근거

ORD 기록
ord-b7a20f3b370d49f79a0e20fdd05b1b08
출처 데이터셋
uspto-grants-1981_08
특허 번호
US04284767

연결된 노트

불러오는 중…