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Sodium Iodide → Benzhydryl 7beta-[2-difluoromethoxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3-(2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate chloride

HRID 1614084
ノート
印刷プレビュー

反応式

HRID 1614084 の反応式
[F:1][CH:2]([F:61])[O:3][N:4]=[C:5]([C:36]1[N:37]=[C:38]([NH:41][C:42]([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[S:39][CH:40]=1)[C:6]([NH:8][C@@H:9]1[C:34](=[O:35])[N:11]2[C:12]([C:18]([O:20][CH:21]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])=[C:13]([CH2:16][Cl:17])[CH2:14][S:15][C@H:10]12)=[O:7].[CH3:62][N:63]1[CH:67]=[CH:66][CH:65]=[N:64]1.[I-].[Na+]>CC(C)=O>[Cl-:17].[F:1][CH:2]([F:61])[O:3][N:4]=[C:5]([C:36]1[N:37]=[C:38]([NH:41][C:42]([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[S:39][CH:40]=1)[C:6]([NH:8][C@@H:9]1[C:34](=[O:35])[N:11]2[C:12]([C:18]([O:20][CH:21]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])=[C:13]([CH2:16][N+:64]3[N:63]([CH3:62])[CH:67]=[CH:66][CH:65]=3)[CH2:14][S:15][C@H:10]12)=[O:7]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 5238Sodium IodideHCID 702551H-Pyrazole, 1-methyl-HCID 131716601Benzhydryl 7beta-[2-(2-tritylaminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate

生成物 1

HCID 178480375Benzhydryl 7beta-[2-difluoromethoxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3-(2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate chloride収率 83.5%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A mixture of benzhydryl 7β-[2-difluoromethoxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3-chloromethyl-3-cephem-4-carboxylate (syn isomer, 8.76 g), N-methylpyrazole (8.76 g), sodium iodide (1.5 g) and acetone (9 ml) was stirred at ambient temperature for 19 hours. The reaction mixture was evaporated, and ethyl acetate (200 ml) and 5% aqueous solution of sodium thiosulfate were added to the residue. The organic layer was separated and tetrahydrofuran (100 ml) was added thereto. The solution was dried over magnesium sulfate and evaporated and the residue was dissolved in a mixture of tetrahydrofuran (200 ml) and water (65 ml). The solution was subjected to column chromatography on an ion-exchange resin "Amberlite IRA-400"(Cl⃝ form), and eluted with a mixture of tetrahydrofuran and water (15:1 V/V). The fractions containing the object compound were collected, combined and evaporated. The residue was triturated with diisopropyl ether to give benzhydryl 7β-[2-difluoromethoxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3-(2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate chloride (syn isomer, 8.0 g).

後処理

  1. customThe reaction mixture was evaporated
  2. additionethyl acetate (200 ml) and 5% aqueous solution of sodium thiosulfate were added to the residue
  3. customThe organic layer was separated
  4. additiontetrahydrofuran (100 ml) was added
  5. dry with materialThe solution was dried over magnesium sulfate
  6. customevaporated
  7. dissolutionthe residue was dissolved in a mixture of tetrahydrofuran (200 ml) and water (65 ml)
  8. washeluted with a mixture of tetrahydrofuran and water (15:1 V/V)
  9. additionThe fractions containing the object compound
  10. customwere collected
  11. customevaporated
  12. customThe residue was triturated with diisopropyl ether

出典と根拠

ORDレコード
ord-f76182323e8d49278ecd050cdbb6451f
出典データセット
uspto-grants-1993_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05194432

反応ノート

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