Hydrochloric Acid → Cefuroxime

HRID 894835

반응식

HRID 894835 반응식
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1/[C:6](=[N:24]/[O:25][CH3:26])/[C:7]([NH:9][C@@H:10]1[C:22](=[O:23])[N:12]2[C:13]([C:19]([OH:21])=[O:20])=[C:14]([CH2:17][OH:18])[CH2:15][S:16][C@H:11]12)=[O:8].ClP([N:31]=[C:32]=[O:33])(Cl)=O.C([O-])(O)=O.[Na+].Cl>O1CCOCC1.ClCCCl.O>[CH3:26][O:25]/[N:24]=[C:6](\[C:7]([NH:9][C@@H:10]1[C:22](=[O:23])[N:12]2[C:13]([C:19]([OH:21])=[O:20])=[C:14]([CH2:17][O:18][C:32]([NH2:31])=[O:33])[CH2:15][S:16][C@H:11]12)=[O:8])/[C:2]1[O:1][CH:5]=[CH:4][CH:3]=1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 70090Phosphorisocyanatidic dichlorideHCID 516892Sodium Bicarbonate2회HCID 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 3

HCID 111,2-Dichloroethane용매HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

A solution of (6R,7R)-7-[Z-2-(fur-2-yl)-2-methoxyiminoacetamido]-3-hydroxymethylceph-3-em-4-carboxylic acid (3.81 g) in dioxan (20 ml) was added over ca. 1 minute to a stirred solution of dichlorophosphinyl isocyanate (1.46 ml) in 1,2-dichloroethane (30 ml) at 19°, the temperature rising to 28°. The resulting solution was stirred for 15 minutes and then added to a solution of NaHCO3 (5.1 g) in water (70 ml). This mixture was stirred at ca. 30° for 1 hour, and then heated at 40° to 45° for a total of 4.5 hours, the pH being adjusted to 5.0 with hydrochloric acid after 3 hours. The two-phase mixture was adjusted from pH 5.8 to 7.0 with aqueous NaHCO3 solution and the aqueous phase was washed with 1,2-dichloroethane (20 ml) and ethyl acetate (50 ml), and 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 extract washed with 25% aqueous sodium chloride solution and evaporated. The solid residue was slurried with diethyl ether to give the title compound (3.18 g, 75.0%); purity by HPLC 91.6% and by TLC 89.5%.

후처리

  1. customrising to 28°
  2. stirringThis mixture was stirred at ca. 30° for 1 hour
  3. temperatureheated at 40° to 45° for a total of 4.5 hours
  4. washthe aqueous phase was washed with 1,2-dichloroethane (20 ml) and ethyl acetate (50 ml)
  5. extractionThe aqueous phase was re-extracted with ethyl acetate
  6. extractionthe combined ethyl acetate extract
  7. washwashed with 25% aqueous sodium chloride solution
  8. customevaporated

출처 및 근거

ORD 기록
ord-8936a1a99bf3491eb063bcb3eba7b72d
출처 데이터셋
uspto-grants-1981_08
특허 번호
US04284767

연결된 노트

불러오는 중…