Chloro-N,N-dimethylformiminium chloride → 7-[2-(2-Cyclopenten-1-yl)oxyimino-2-(2-formamidothiazol-4-yl)acetamido]-2-methyl-3-cephem-4-carboxylic acid

HRID 1074939노트

반응식

HRID 1074939 반응식
[CH:1]1([O:6][N:7]=[C:8]([C:12]2[N:13]=[C:14]([NH:17][CH:18]=[O:19])[S:15][CH:16]=2)[C:9]([OH:11])=O)[CH2:5][CH2:4][CH:3]=[CH:2]1.C[N+](C)=CCl.[Cl-].[NH2:26][CH:27]1[C:38](=[O:39])[N:29]2[C:30]([C:35]([OH:37])=[O:36])=[CH:31][CH:32]([CH3:34])[S:33][C@H:28]12.C[Si](CC(N)=O)(C)C>O1CCCC1.C(OCC)(=O)C.O>[CH:1]1([O:6][N:7]=[C:8]([C:12]2[N:13]=[C:14]([NH:17][CH:18]=[O:19])[S:15][CH:16]=2)[C:9]([NH:26][CH:27]2[C:38](=[O:39])[N:29]3[C:30]([C:35]([OH:37])=[O:36])=[CH:31][CH:32]([CH3:34])[S:33][C@H:28]23)=[O:11])[CH2:5][CH2:4][CH:3]=[CH:2]1

참가 물질

8

반응물 4

HCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 357676Acetamide, 2-(trimethylsilyl)-HCID 128022512-Methyl-7-amino-3-cephem-4-carboxylic acidHCID 538228722-(2-Cyclopenten-1-yl)oxyimino-2-(2-formamidothiazol-4-yl)acetic acid

생성물 1

HCID 1317130257-[2-(2-Cyclopenten-1-yl)oxyimino-2-(2-formamidothiazol-4-yl)acetamido]-2-methyl-3-cephem-4-carboxylic acid수율 77.8%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매2회

실험 절차

A solution of 2-(2-cyclopenten-1-yl)oxyimino-2-(2-formamidothiazol-4-yl)acetic acid (syn isomer) (1.5 g) in dry tetrahydrofuran (12 ml) was added to the stirred suspension of the solution of Vilsmeier reagent under ice-cooling. The resulting mixture was added to a solution of 7-amino-2-methyl-3-cephem-4-carboxylic acid (1.37 g) and trimethylsilylacetamide (5.04 g) in ethyl acetate (14 ml) at -30° to -20° C. and the mixture was stirred at -5°~-10° C. for 2 hours. After the addition of water and ethyl acetate to the reaction mixture, the ethyl acetate layer was separated and adjusted to pH 7 with an aqueous solution of sodium bicarbonate. The aqueous layer was separated and thereto was added ethyl acetate. The mixture was adjusted to pH 2.5 with 10% hydrochloric acid. The ethyl acetate layer was separated, washed with an aqueous solution of sodium chloride, dried over magnesium sulfate and then evaporated. The residue was pulverized in diisopropyl ether to give 7-[2-(2-cyclopenten-1-yl)oxyimino-2-(2-formamidothiazol-4-yl)acetamido]-2-methyl-3-cephem-4-carboxylic acid (syn isomer) (1.98 g).

후처리

  1. temperaturecooling
  2. customthe ethyl acetate layer was separated
  3. customThe aqueous layer was separated
  4. additionwas added ethyl acetate
  5. customThe ethyl acetate layer was separated
  6. washwashed with an aqueous solution of sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. customevaporated

출처 및 근거

ORD 기록
ord-17f347830ccc46768070c1b54a100b40
출처 데이터셋
uspto-grants-1983_07
특허 번호
US04394384

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