Hydrochloric Acid → Cefuroxime

HRID 894832

반응식

HRID 894832 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)=O.[Na+].Cl.[OH-].[Na+]>C(#N)C.O.C(O)(=O)C.CO.C(Cl)(Cl)Cl>[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

11

반응물 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70090Phosphorisocyanatidic dichlorideHCID 516892Sodium BicarbonateHCID 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 5479529Cefuroxime수율 75%

시약·촉매·용매 5

HCID 176Acetic Acid용매HCID 887Methanol용매HCID 962Water용매HCID 6212Chloroform용매HCID 6342Acetonitrile용매

실험 절차

Dichlorophosphinyl isocyanate (1.46 ml) was added to a stirred suspension of (6R,7R)-7-[Z-2-(fur-2-yl)-2-methoxyiminoacetamido]-3-hydroxymethylceph-3-em-4-carboxylic acid (3.81 g) in acetonitrile (50 ml) cooled to 5°. The reaction mixture was stirred at 5° for 15 minutes and then added to a solution of NaHCO3 (5.1 g) in water (100 ml). This mixture was stirred for 10 minutes when the pH was adjusted from 7.4 to 5.0 with hydrochloric acid. The pH fell to 3.0 after a further 10 minutes so it was readjusted to 5.0 with aqueous sodium hydroxide solution. The mixture was kept at ca. 20° overnight and then heated at 45° for 2 hours when TLC (chloroform:methanol:acetic acid=9:2:1) showed that reaction was essentially complete. The precipitated white solid was removed by filtration and the filtrate was washed with ethyl acetate. The aqueous phase was acidified to pH 1.9 with dilute hydrochloric acid in the presence of ethyl acetate. The aqueous phase was re-extracted with ethyl acetate, and the combined ethyl acetate extracts were washed with 25% aqueous sodium chloride solution and then evaporated. The solid residue was triturated with diethyl ether to give the title compound (3.18 g, 75.0%), purity by HPLC 95.4% and by TLC 91%.

후처리

  1. temperaturecooled to 5°
  2. stirringThis mixture was stirred for 10 minutes when the pH
  3. waitThe pH fell to 3.0 after a further 10 minutes so it
  4. waitThe mixture was kept at ca. 20° overnight
  5. customshowed that reaction
  6. customThe precipitated white solid was removed by filtration
  7. washthe filtrate was washed with ethyl acetate
  8. extractionThe aqueous phase was re-extracted with ethyl acetate
  9. washthe combined ethyl acetate extracts were washed with 25% aqueous sodium chloride solution
  10. customevaporated
  11. customThe solid residue was triturated with diethyl ether

출처 및 근거

ORD 기록
ord-1cad6ea37adf4ef9b6d06601bb629461
출처 데이터셋
uspto-grants-1981_08
특허 번호
US04284767

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