Tetrahydrofuran → 3-Iodomethylcephem

HRID 255474노트

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HRID 255474 반응식
NC1SC=C(C(=NOCC2C=CC(Cl)=CC=2)C(N[C@@H:11]2[C:26](=[O:27])[N:13]3[C:14](C(O)=O)=[C:15]([CH2:18]OC(=O)C)[CH2:16][S:17][C@H:12]23)=O)N=1.CN([Si](C)(C)C)C(C(F)(F)F)=O.[Si]([I:54])(C)(C)C.C1COCC1>C(Cl)Cl>[I:54][CH2:18][C:15]1[CH2:16][S:17][C@@H:12]2[CH2:11][C:26](=[O:27])[N:13]2[CH:14]=1

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 32510N-methyl-N-(trimethylsilyl)trifluoroacetamideHCID 85247Trimethylsilyl iodideHCID 1317152757beta-[2-(2-Aminothiazol-4-yl)-2-(4-chlorobenzyloxyimino)acetamido]-3-acetoxymethyl-3-cephem-4-carboxylic acid

생성물 1

HCID 690682033-Iodomethylcephem

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
40 °C

실험 절차

To a suspension of 200 mg (0.35 mmole) of 7β-[2-(2-aminothiazol-4-yl)-2-(4-chlorobenzyloxyimino)acetamido]-3-acetoxymethyl-3-cephem-4-carboxylic acid in 5 ml of methylene chloride was added 0.5 ml of MSTFA and the suspension was stirred at 40° C. until solution occurred. The solution was cooled to room temperature and 0.13 ml (0.87 mmole) of TMSI was added. The reaction stirred at room temperature for 30 minutes and evaporated to an oil. The oil was dissolved in 3 ml of acetonitrile and 0.12 ml (1.5 mmole) of THF was added. The mixture was then stirred at room temperature for 5 minutes to destroy excess TMSI and provide in solution the corresponding 3-iodomethyl-3-cephem derivative.

후처리

  1. temperatureThe solution was cooled to room temperature
  2. stirringThe reaction stirred at room temperature for 30 minutes
  3. customevaporated to an oil
  4. dissolutionThe oil was dissolved in 3 ml of acetonitrile
  5. stirringThe mixture was then stirred at room temperature for 5 minutes
  6. customto destroy excess TMSI

출처 및 근거

ORD 기록
ord-a70f58c51dbe4e83bb5f58d4dea3b94d
출처 데이터셋
uspto-grants-1987_10
특허 번호
US04698338

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