Hydrochloric Acid → Chloro-N,N-dimethylformiminium chloride

HRID 1463071ノート

反応式

HRID 1463071 の反応式
P(Cl)(Cl)([Cl:3])=O.[C:6]([O:10][C:11]([CH2:13][O:14][N:15]=[C:16]([C:20]1[N:24]=[CH:23][S:22][N:21]=1)[C:17]([OH:19])=O)=[O:12])([CH3:9])([CH3:8])[CH3:7].[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:42]=[CH:43][C:44]4[N:45]([N:47]=[N:48][N:49]=4)[N:46]=3)[CH2:37][S:38][C@H:33]12.C(=O)(O)[O-].[Na+].C(=O)([O-])[O-].[Na+].[Na+].Cl>C(OCC)(=O)C.O.CC(C)=O.CN(C)C=O>[CH3:25][N+:26]([CH3:29])=[CH:27][Cl:28].[Cl-:3].[C:6]([O:10][C:11]([CH2:13][O:14][N:15]=[C:16]([C:20]1[N:24]=[CH:23][S:22][N:21]=1)[C:17]([NH: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:42]=[CH:43][C:44]4[N:45]([N:47]=[N:48][N:49]=4)[N:46]=3)[CH2:37][S:38][C@H:33]12)=[O:19])=[O:12])([CH3:7])([CH3:8])[CH3:9]

参加物

13

反応物 7

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 516892Sodium BicarbonateHCID 13345661HCID 13345661、化合物HCID 539872492-Tert-butoxycarbonylmethoxyimino-2-(1,2,4-thiadiazol-3-yl)acetic acid

生成物 2

HCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 1317136127-[2-t-Butoxycarbonylmethoxyimino-2-(1,2,4-thiadiazol-3-yl)acetamido]-3-(tetrazolo[1,5-b]pyridazin-6-yl)thiomethyl-3-cephem-4-carboxylic acid

試薬・触媒・溶媒 4

HCID 180Acetone溶媒HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒3 回

実験手順

Vilsmeier reagent was prepared from phosphorus oxychloride (1.4 g) and N,N-dimethylformamide (0.65 g) in ethyl acetate (2.6 ml) in a usual manner. 2-t-Butoxycarbonylmethoxyimino-2-(1,2,4-thiadiazol-3-yl)acetic acid (syn isomer) (2.1 g) was added to the stirred suspension of Vilsmeier reagent in ethyl acetate (20 ml) under ice-cooling and the mixture was stirred for 30 minutes at the same temperature to prepare an activated acid solution. 7-Amino-3-(tetrazolo[1,5-b]pyridazin-6-yl)thiomethyl-3-cephem-4-carboxylic acid (3.0 g) was dissolved to the solution of sodium bicarbonate (2.1 g) in water (25 ml) and acetone (25 ml). To the solution was added the above activated acid solution at -3° to 3° C. and the solution was stirred for 30 minutes under keeping the pH 7 to 8 with 20% an aqueous solution of sodium carbonate. Ethyl acetate and water were added to the reaction mixture and the mixture was adjusted to pH 2.0 with 10% hydrochloric acid. The separated organic layer was washed with saturated aqueous solution of sodium chloride, dried over magnesium sulfate and evaporated to give 7-[2-t-butoxycarbonylmethoxyimino-2-(1,2,4-thiadiazol-3 -yl)acetamido]-3-(tetrazolo[1,5-b]pyridazin-6-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (4.07 g).

後処理

  1. temperaturecooling
  2. customto prepare an activated acid solution
  3. additionTo the solution was added the above activated acid solution at -3° to 3° C.
  4. stirringthe solution was stirred for 30 minutes
  5. washThe separated organic layer was washed with saturated aqueous solution of sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. customevaporated

出典と根拠

ORDレコード
ord-8c6b11bc267543108f19214b61b2b24a
出典データセット
uspto-grants-1984_07
特許番号
US04463003

反応ノート

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