Tetrahydrofuran → 3-Iodomethylcephem

HRID 255474ノート

反応式

HRID 255474 の反応式
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

参加物

6

反応物 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

生成物 1

HCID 690682033-Iodomethylcephem

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
40 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a70f58c51dbe4e83bb5f58d4dea3b94d
出典データセット
uspto-grants-1987_10
特許番号
US04698338

反応ノート

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