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

HRID 28278

反応式

HRID 28278 の反応式
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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 5943Carbon Tetrachloride溶媒

実験手順

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 2 N 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.).

後処理

  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 2 N 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

出典と根拠

ORDレコード
ord-370648710a9249b28d3f4a5c3382e888
出典データセット
uspto-grants-1980_09
特許番号
US04225707

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