Dimethylformamide → 2-Cephem

HRID 127650Notes

Reaction equation

HRID 127650 reaction equation
C[Si](C)(C)Cl.[SH:6][C:7]1N(C)N=NN=1.[CH2:13]([N:15]([CH:19]([CH3:21])C)[CH:16]([CH3:18])C)C.CN(C)C=[O:25]>C(OCC)(=O)C>[S:6]1[C@@H:16]2[CH2:18][C:13](=[O:25])[N:15]2[CH2:19][CH:21]=[CH:7]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6397ChlorotrimethylsilaneHCID 81531DiisopropylethylamineHCID 178482017HCID 178482017, compound

Product 1

HCID 714080692-Cephem

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

0.049 ml (0.388 mmol) of trimethylchlorosilane, 0.585 g (5.05 mmols) of 5-mercapto-1-methyltetrazole and 0.935 ml (5.43 mmols) of N-ethyl-N,N-diisopropylamine are added to a solution of 2.93 g (3.82 mmols) of 7β-(D-α-tert.butoxycarbonylamino-α-phenyl-acetylamino)-3-(p-toluenesulphonyloxy)-3-cephem-4-carboxylic acid diphenylmethyl ester in 11 ml of dimethylformamide. The red-brown solution is stirred for 16 hours at room temperature under nitrogen, diluted with ethyl acetate and purified by shaking with water, saturated aqueous sodium bicarbonate solution, 1 M sulphuric acid and saturated aqueous sodium chloride solution. The organic phase is dried over sodium sulphate and evaporated in vacuo. After drying the residue in a high vacuum, a mixture consisting of 7β-(D-α-tert.butoxycarbonylamino)-α-phenyl-acetylamino) 3-(1-methyl-5-tetrazolylthio)-3-cephem-4-carboxylic acid diphenylmethyl ester and the corresponding isomeric 2-cephem compound results and shows 2 spots in a thin layer chromatogram: silica gel (toluene/ethyl acetate, 2:1): Rf=0.13 (3-cephem compound); Rf=0.07 (2-cephem compound); IR spectrum of the crude product (CHCl3): characteristic bands at 3400, 1780, 1730-1690 (broad), 1495 and 1370 cm-1.

Workup

  1. custompurified
  2. stirringby shaking with water, saturated aqueous sodium bicarbonate solution, 1 M sulphuric acid and saturated aqueous sodium chloride solution
  3. dry with materialThe organic phase is dried over sodium sulphate
  4. customevaporated in vacuo
  5. customAfter drying the residue in a high vacuum

Sources & evidence

ORD record
ord-daa6e7ea4e324253a494500e3863bc0c
Source dataset
uspto-grants-1981_03
Patent number
US04256739

Reaction notes

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