Triethylamine → Benzhydryl 7-formamido-3-hydroxy-3-cephem-4-carboxylate

HRID 704260노트

반응식

HRID 704260 반응식
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH:14]([NH:16][CH:17]1[C:41](=[O:42])[N:19]2[CH:20]([C:25]([O:27][CH:28]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:26])[CH:21]([OH:24])[CH2:22][S:23][C@H:18]12)=[O:15].C(N(CC)CC)C>C(Cl)Cl.CS(C)=O>[CH:14]([NH:16][CH:17]1[C:41](=[O:42])[N:19]2[C:20]([C:25]([O:27][CH:28]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[O:26])=[C:21]([OH:24])[CH2:22][S:23][C@H:18]12)=[O:15]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 86743417Benzhydryl 7-formamido-3-hydroxycepham-4-carboxylate

생성물 1

HCID 88528581Benzhydryl 7-formamido-3-hydroxy-3-cephem-4-carboxylate수율 83.4%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매2회HCID 6344Dichloromethane용매3회

반응 조건

온도
-50 °C

실험 절차

A solution of trifluoroacetic anhydride (2.12 ml) in methylene chloride (5 ml) was added dropwise to a solution of dimethyl sulfoxide (1.56 g) in methylene chloride (10 ml) at -50° C. The mixture was stirred at -50° C. for 10 minutes. To the mixture was added a solution of benzhydryl 7-formamido-3-hydroxycepham-4-carboxylate (4.12 g) in methylene chloride (10 ml) and dimethyl sulfoxide (1 ml). The mixture was stirred at -50° C. for 30 minutes and triethylamine (4 ml) was added dropwise thereto at -50° C. The reaction mixture was allowed to warm up to ambient temperature, poured into ice-water and extracted with methylene chloride. The extract was washed three times with water, dried over magnesium sulfate and filtered, and the filtrate was evaporated in vacuo The residue was triturated with diisopropyl ether to give benzhydryl 7-formamido-3-hydroxy-3-cephem-4-carboxylate (3.42 g) as powder.

후처리

  1. stirringThe mixture was stirred at -50° C. for 30 minutes
  2. customat -50° C
  3. temperatureto warm up to ambient temperature
  4. extractionextracted with methylene chloride
  5. washThe extract was washed three times with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customthe filtrate was evaporated in vacuo The residue
  9. customwas triturated with diisopropyl ether

출처 및 근거

ORD 기록
ord-8219465ceaa447e9920fcd19eb2e1f2b
출처 데이터셋
uspto-grants-1991_01
특허 번호
US04985555

반응 노트

불러오는 중…