Phosphorus oxychloride → Chloro-N,N-dimethylformiminium chloride

HRID 371242ノート

反応式

HRID 371242 の反応式
P(Cl)(Cl)([Cl:3])=O.[CH:6]1([O:11][N:12]=[C:13]([C:17]2[N:18]=[C:19]([NH:22][CH:23]=[O:24])[S:20][CH:21]=2)[C:14]([OH:16])=O)[CH2:10][CH2:9][CH:8]=[CH:7]1.[CH3:25][N+:26]([CH3:29])=[CH:27][Cl:28].[Cl-].[NH2:31][CH:32]1[C:53](=[O:54])[N:34]2[C:35]([C:50]([OH:52])=[O:51])=[C:36]([CH2:39][S:40][C:41]3[CH:46]=[C:45]([C:47]([OH:49])=[O:48])[CH:44]=[CH:43][N:42]=3)[CH2:37][S:38][C@H:33]12.C(=O)(O)[O-].[Na+]>O1CCCC1.CC(C)=O.O>[CH3:25][N+:26]([CH3:29])=[CH:27][Cl:28].[Cl-:3].[CH:6]1([O:11][N:12]=[C:13]([C:17]2[N:18]=[C:19]([NH:22][CH:23]=[O:24])[S:20][CH:21]=2)[C:14]([NH:31][CH:32]2[C:53](=[O:54])[N:34]3[C:35]([C:50]([OH:52])=[O:51])=[C:36]([CH2:39][S:40][C:41]4[CH:46]=[C:45]([C:47]([OH:49])=[O:48])[CH:44]=[CH:43][N:42]=4)[CH2:37][S:38][C@H:33]23)=[O:16])[CH2:10][CH2:9][CH:8]=[CH:7]1

参加物

10

反応物 5

HCID 24813Phosphorus oxychlorideHCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 516892Sodium BicarbonateHCID 538228722-(2-Cyclopenten-1-yl)oxyimino-2-(2-formamidothiazol-4-yl)acetic acidHCID 704870447-Amino-3-(4-carboxypyridin-2-yl)thiomethyl-3-cephem-4-carboxylic acid

生成物 2

HCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 1317142777-[2-(2-Cyclopenten-1-yl)oxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(4-carboxypyridin-2-yl)thiomethyl-3-cephem-4-carboxylic acid

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

The solution of Vilsmeier reagent was prepared from dry N,N-dimethylformamido (0.475 g) and phosphoryl chloride (0.997 g) in dry tetrahydrofuran (1 ml) in a usual manner. A solution of 2-(2-cyclopenten-1-yl)oxyimino-2-(2-formamidothiazol-4-yl)acetic acid (syn isomer) (1.91 g) in dry tetrahydrofuran (12 ml) was added to the stirred suspension of the solution of Vilsmeier reagent at 0° to 5° C. and the mixture was stirred for 20 minutes. The resulting mixture was added to a solution of 7-amino-3-(4-carboxypyridin-2-yl)thiomethyl-3-cephem-4-carboxylic acid (1.84 g) and sodium bicarbonate (0.84 g) in a mixture of acetone (12 ml) and water (12 ml) at -3° to 0° C. and the mixture was stirred at the same temperature for 40 minutes. The reaction mixture was evaporated under reduced pressure. The residue was adjusted to pH 6.5 with 10% hydrochloric acid, washed with ethyl acetate, concentrated to a small volume and then adjusted to pH 2.9 with 10% hydrochloric acid. The precipitates were collected by filtration, washed with water and dried over phosphorus pentoxide to give 7-[2-(2-cyclopenten-1-yl)oxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(4-carboxypyridin-2-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (2.74 g).

後処理

  1. stirringthe mixture was stirred at the same temperature for 40 minutes
  2. customThe reaction mixture was evaporated under reduced pressure
  3. washwashed with ethyl acetate
  4. concentrationconcentrated to a small volume
  5. filtrationThe precipitates were collected by filtration
  6. washwashed with water
  7. dry with materialdried over phosphorus pentoxide

出典と根拠

ORDレコード
ord-968840a1a7544634b72650258942a56a
出典データセット
uspto-grants-1985_07
特許番号
US04529802

反応ノート

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