Bromhydrol → HCID 12834047、化合物

HRID 1763999ノート

反応式

HRID 1763999 の反応式
[CH3:1][C:2]12[CH2:15][C:6]1([C:7]([O:9][CH2:10][C:11]([Cl:14])([Cl:13])[Cl:12])=[O:8])[N:5]1[C:16](=[O:29])[CH:17]([NH:18][C:19](=[O:28])[CH2:20][O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C@H:4]1[S:3]2.[Br-].[Al+3].[Br-].[Br-]>ClCCl>[CH3:1][CH:2]1[CH:15]=[C:6]([C:7]([O:9][CH2:10][C:11]([Cl:13])([Cl:12])[Cl:14])=[O:8])[N:5]2[C:16](=[O:29])[CH:17]([NH:18][C:19](=[O:28])[CH2:20][O:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C@H:4]2[S:3]1

参加物

4

反応物 2

HCID 166749BromhydrolHCID 70528477HCID 70528477、化合物

生成物 1

HCID 12834047HCID 12834047、化合物収率 64.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 2,2,2-trichloroethyl 2-methyl-2,3-methylene-6-(2-phenoxyacetamido)penam-3-carboxylate (1.39 g.) in dried dichloromethane (7 ml.) was dropwise added over 10 minutes at -10° C. to a solution of aluminum bromide (1.16 g.) in dried dichloromethane (12 ml.), and the reaction temperature was gradually elevated to room temperature, after which the mixture was stirred for 4 hours at room temperature. After the reaction, the reaction mixture was poured into ice-water (70 ml.) and the dichloromethane layer was separated, after which the aqueous layer was once extracted with chloroform. The combined dichloromethane and chloroform layer was washed in turn with water, 2% hydrochloric acid, water, a dilute sodium bicarbonate aqueous solution and water, and then dried over magnesium sulfate. After the solvent was distilled off, the obtained pale brown oil (1.2 g.) was crystallized by adding ether and a small amount of isopropyl ether. The crystals were collected by filtration, followed by washing with isopropyl ether and recrystallized from a mixture of benzene: isopropyl ether (1:3) to give colorless granules of 2,2,2-trichloroethyl 2-methyl-7-(2-phenoxyacetamido)-3-cephem-4-carboxylate (0.9 g.), mp 118° to 120° C.

後処理

  1. customwas gradually elevated to room temperature
  2. customAfter the reaction
  3. customthe dichloromethane layer was separated
  4. extractionafter which the aqueous layer was once extracted with chloroform
  5. washThe combined dichloromethane and chloroform layer was washed in turn with water, 2% hydrochloric acid, water
  6. dry with materiala dilute sodium bicarbonate aqueous solution and water, and then dried over magnesium sulfate
  7. distillationAfter the solvent was distilled off
  8. customthe obtained pale brown oil (1.2 g.) was crystallized
  9. additionby adding ether
  10. filtrationThe crystals were collected by filtration
  11. washby washing with isopropyl ether
  12. customrecrystallized from a mixture of benzene: isopropyl ether (1:3)

出典と根拠

ORDレコード
ord-810eeb38215e4583aa22b35f5faa6596
出典データセット
uspto-grants-1978_09
特許番号
US04113940

反応ノート

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