Hydrochloric Acid → Chloro-N,N-dimethylformiminium chloride

HRID 1463071노트

반응식

HRID 1463071 반응식
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]

참가 물질

13

반응물 7

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

생성물 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

시약·촉매·용매 4

HCID 180Acetone용매HCID 962Water용매2회HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매3회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8c6b11bc267543108f19214b61b2b24a
출처 데이터셋
uspto-grants-1984_07
특허 번호
US04463003

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