Tetrahydrofuran → 3-Iodomethylcephem
Reaction equation
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]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
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.
Workup
- temperatureThe solution was cooled to room temperature
- stirringThe reaction stirred at room temperature for 30 minutes
- customevaporated to an oil
- dissolutionThe oil was dissolved in 3 ml of acetonitrile
- stirringThe mixture was then stirred at room temperature for 5 minutes
- customto destroy excess TMSI
Sources & evidence
- ORD record
- ord-a70f58c51dbe4e83bb5f58d4dea3b94d
- Source dataset
- uspto-grants-1987_10
- Patent number
- US04698338
Reaction notes
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