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Sodium Carbonate → 4-Nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-n-butoxyiminoacetamido]3-cephem-4-carboxylate

HRID 364538
ノート
印刷プレビュー

反応式

HRID 364538 の反応式
P(Cl)(Cl)(Cl)=O.[CH:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[N:18][O:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:15]([OH:17])=O)[N:13]=1)=[O:7].[NH2:24][CH:25]1[C:45](=[O:46])[N:27]2[C:28]([C:32]([O:34][CH2:35][C:36]3[CH:41]=[CH:40][C:39]([N+:42]([O-:44])=[O:43])=[CH:38][CH:37]=3)=[O:33])=[CH:29][CH2:30][S:31][C@H:26]12.C(=O)([O-])[O-].[Na+].[Na+]>O.CC(C)=O.O1CCCC1.CN(C)C=O>[CH:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[N:18][O:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:15]([NH:24][CH:25]2[C:45](=[O:46])[N:27]3[C:28]([C:32]([O:34][CH2:35][C:36]4[CH:37]=[CH:38][C:39]([N+:42]([O-:44])=[O:43])=[CH:40][CH:41]=4)=[O:33])=[CH:29][CH2:30][S:31][C@H:26]23)=[O:17])[N:13]=1)=[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

9

反応物 4

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 12775080p-Nitrobenzyl 7-amino-3-cephem-4-carboxylateHCID 541324842-(2-Formamidothiazol-4-yl)-2-butoxyiminoacetic acid

生成物 1

HCID 1317124564-Nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-n-butoxyiminoacetamido]3-cephem-4-carboxylate収率 81.8%

試薬・触媒・溶媒

4
HCID 180Acetone溶媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒3 回

実験手順

Phosphoryl chloride (13.2 g.) was added dropwise to a stirred solution of N,N-dimethylformamide (6.3 g.) and tetrahydrofuran (24.7 ml.) at -5° C., and stirred at the same temperature for 30 minutes. Tetrahydrofuran (120 ml.) and 2-(2-formamidothiazol-4-yl)-2-n-butoxyiminoacetic acid (syn isomer, 19.5 g.) were added to the solution at -5° C., and stirred at the same temperature for 30 minutes. The solution was added dropwise a stirred suspension of 4-nitrobenzyl 7-amino-3-cephem-4-carboxylate (24.7 g.), tetrahydrofuran (120 ml.), acetone (60 ml.) and water (60 ml.) at -5° to 5° C. over 15 minutes while adjusting to pH 7 to 7.5 with 20% aqueous solution of sodium carbonate, and then the solution was stirred for 30 minutes. The insoluble substance was filtered off, and a saturated aqueous solution of sodium chloride was added to the filtrate. The solution was extracted with tetrahydrofuran twice. The extract was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated in vacuo. The residue was triturated with diisopropyl ether to give 4-nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-n-butoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer, 34.6 g.).

後処理

  1. stirringstirred at the same temperature for 30 minutes
  2. additionThe solution was added dropwise
  3. stirringthe solution was stirred for 30 minutes
  4. filtrationThe insoluble substance was filtered off
  5. additiona saturated aqueous solution of sodium chloride was added to the filtrate
  6. extractionThe solution was extracted with tetrahydrofuran twice
  7. washThe extract was washed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe residue was triturated with diisopropyl ether

出典と根拠

ORDレコード
ord-b803f564a3784f7c923adaf8745f2644
出典データセット
uspto-grants-1986_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04604456

反応ノート

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