Dichloromethane → 2,2,2-Trichloroethyl 2-methyl-7-(3-oxo-4-bromobutyramido)-3-cephem-4-carboxylate

HRID 261842노트

반응식

HRID 261842 반응식
Cl.[CH3:2][CH:3]1[CH:8]=[C:7]([C:9]([O:11][CH2:12][C:13]([Cl:16])([Cl:15])[Cl:14])=[O:10])[N:6]2[C:17](=[O:20])[CH:18]([NH2:19])[C@H:5]2[S:4]1.C[Si](CC(N)=O)(C)C.C(Cl)Cl.[O:32]=[C:33]([CH2:38][Br:39])[CH2:34][C:35](Br)=[O:36]>C(Cl)(Cl)(Cl)Cl.O>[CH3:2][CH:3]1[CH:8]=[C:7]([C:9]([O:11][CH2:12][C:13]([Cl:16])([Cl:14])[Cl:15])=[O:10])[N:6]2[C:17](=[O:20])[CH:18]([NH:19][C:35](=[O:36])[CH2:34][C:33](=[O:32])[CH2:38][Br:39])[C@H:5]2[S:4]1

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 357676Acetamide, 2-(trimethylsilyl)-HCID 128310484-Bromo-3-oxobutanoyl bromideHCID 128341352,2,2-Trichloroethyl 2-methyl-7-amino-3-cephem-4-carboxylate hydrochloride

생성물 1

HCID 1317114902,2,2-Trichloroethyl 2-methyl-7-(3-oxo-4-bromobutyramido)-3-cephem-4-carboxylate

시약·촉매·용매 2

HCID 962Water용매HCID 5943Carbon Tetrachloride용매

실험 절차

A mixture of 2,2,2-trichloroethyl 2-methyl-7-amino-3-cephem-4-carboxylate hydrochloride (0.38 g.), trimethylsilylacetamide (1.1 g.) and methylene chloride (10 ml.) was stirred for 30 minutes at room temperature, and thus obtained solution was cooled to -15° C. To the solution was added dropwise 3-oxo-4-bromobutyryl bromide (1.0 m mole) in carbon tetrachloride (13 ml.) under cooling to -15° C., and the mixture was stirred for 1.5 hours at the same temperature and for 30 minutes without external cooling. The mixture was poured into cold water, and then the organic layer was separated therefrom. The organic layer was washed with 2N hydrochloric acid (8 ml ×3) and water (10 ml ×2) in turn, dried over magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure. The residue was pulverized in diisopropyl ether, collected by filtration and then dried to give pale brown powder of 2,2,2-trichloroethyl 2-methyl-7-(3-oxo-4-bromobutyramido)-3-cephem-4-carboxylate (0.31 g.), mp 78° to 83° C. (dec.).

후처리

  1. temperaturethus obtained solution was cooled to -15° C
  2. temperatureunder cooling to -15° C.
  3. stirringthe mixture was stirred for 1.5 hours at the same temperature and for 30 minutes without external cooling
  4. customthe organic layer was separated
  5. washThe organic layer was washed with 2N hydrochloric acid (8 ml ×3) and water (10 ml ×2) in turn
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. filtrationcollected by filtration
  10. customdried

출처 및 근거

ORD 기록
ord-7d60be4214084bcea0b29baf97ebdeff
출처 데이터셋
uspto-grants-1979_05
특허 번호
US04152433

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