Hydrochloric Acid → Chloro-N,N-dimethylformiminium chloride

HRID 462596ノート

反応式

HRID 462596 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:21]=[CH:22][S:23][CH:24]=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-].C[Si](CC(N)=O)(C)C.[NH2:39][CH:40]1[C:50](=[O:51])[N:42]2[C:43]([C:47]([OH:49])=[O:48])=[CH:44][CH2:45][S:46][C@H:41]12.C(=O)([O-])[O-].[K+].[K+].Cl>C(OCC)(=O)C.O1CCCC1.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:21]=[CH:22][S:23][CH:24]=1)[C:17]([NH:39][CH:40]1[C:50](=[O:51])[N:42]2[C:43]([C:47]([OH:49])=[O:48])=[CH:44][CH2:45][S:46][C@H:41]12)=[O:19])=[O:12])([CH3:7])([CH3:8])[CH3:9]

参加物

13

反応物 7

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 357676Acetamide, 2-(trimethylsilyl)-HCID 12941984(6R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidHCID 544727372-t-Butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetic acid

生成物 2

HCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 1317142047-[2-t-Butoxycarbonylmethoxyimino2-(4-thiazolyl)acetamido]-3-cephem-4-carboxylic acid

試薬・触媒・溶媒 4

HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

Vilsmeier reagent was prepared from phosphorus oxychloride (0.76 g) and N,N-dimethylformamide (0.36 g) in ethyl acetate (1.44 ml) in a usual manner. 2-t-Butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetic acid (syn isomer) (1.2 g) was added to the stirred suspension of Vilsmeier reagent in ethyl acetate (20 ml) under ice-cooling and the mixture was stirred for 20 minutes at the same temperature to prepare an activated acid solution. Trimethylsilylacetamide (3.5 g) was added to the stirred suspension of 7-amino-3-cephem-4-carboxylic acid (0.76 g) in tetrahydrofuran (15 ml) and the mixture was stirred for 20 minutes at 35° to 40° C. To the solution was added the above activated acid solution at -10° C. and the mixture was stirred for 30 minutes at the same temperature. Water was added to the reaction mixture and the separated organic layer was added to water and the mixture was adjusted to pH 7.5 with saturated aqueous solution of potassium carbonate. The separated aqueous layer was adjusted to pH 2.0 with 10% hydrochloric acid and extracted with ethyl acetate. The extracted layer was washed with saturated aqueous solution of sodium chloride, dried over magnesium sulfate and evaporated to give 7-[2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetamido]-3-cephem-4-carboxylic acid (syn isomer) (1.4 g).

後処理

  1. temperaturecooling
  2. customto prepare an activated acid solution
  3. stirringthe mixture was stirred for 20 minutes at 35° to 40° C
  4. additionTo the solution was added the above activated acid solution at -10° C.
  5. stirringthe mixture was stirred for 30 minutes at the same temperature
  6. extractionextracted with ethyl acetate
  7. washThe extracted layer was washed with saturated aqueous solution of sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. customevaporated

出典と根拠

ORDレコード
ord-691a3709739d4c4dab3ba3616f0e6783
出典データセット
uspto-grants-1985_05
特許番号
US04515788

反応ノート

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