Water → HCID 67947947, compound

HRID 1032851Notes

Reaction equation

HRID 1032851 reaction equation
[NH2:1][CH:2]1[C:19](=[O:20])[N:4]2[C:5]([C:16]([OH:18])=[O:17])=[C:6]([CH2:9][S:10][C:11]3[S:15][N:14]=[N:13][CH:12]=3)[CH2:7][S:8][C@H:3]12.C(N(CC)CC)C.[CH3:28][Si:29]([CH2:32][CH2:33][O:34][CH2:35]Cl)([CH3:31])[CH3:30].O>CN(C)C=O>[NH2:1][CH:2]1[C:19](=[O:20])[N:4]2[C:5]([C:16]([O:18][CH2:35][O:34][CH2:33][CH2:32][Si:29]([CH3:31])([CH3:30])[CH3:28])=[O:17])=[C:6]([CH2:9][S:10][C:11]3[S:15][N:14]=[N:13][CH:12]=3)[CH2:7][S:8][C@H:3]12

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 67887250HCID 67887250, compound

Product 1

HCID 67947947HCID 67947947, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-amino-3-[(1,2,3-thiadiazol-5-yl)thiomethyl]ceph-3-em-4-carboxylic acid (3.30 g, 10 mmol.) and triethylamine (1.40 ml, 10 mmol.) in 50 ml of dimethylformamide was stirred at room temperature for 1 0 hour. Trimethylsilylethoxymethyl chloride (1.80 ml, 10 mmol.) was added dropwise, the reaction mixture was stirred for 15 minutes at room temperature then poured into 100 ml of water and extracted with 80 ml of ethyl acetate. The ethyl acetate extract was washed with 75 ml aliquots of saturated sodium bicarbonate, water and brine then dried over magnesium sulfate. Evaporation of the solvent afforded 3.05 g of product as an amber oil: NMR (CDCl3) δ 0.03 [S, 9H, Si(CH3)3 ], 0.95 (t, 2H, J=7.5 Hz, --CH2Si), 2.00 (S, 2H, NH2), 3.50 (m, 4H, --OCH2Si and indocyclic --CH 2 --S--), 4.00 (S, 2H, oxocyclic --CH2S--), 4.60 (d, 1H, J=5.0 Hz, 6H of 7ACA), 4.80 (d, 1H, J=5.0 Hz, 7H of 7ACA), 5.30 (S, 2H, --OCH2O--), 8.40 (S, 1H, thiadiazole H).

Workup

  1. stirringthe reaction mixture was stirred for 15 minutes at room temperature
  2. extractionextracted with 80 ml of ethyl acetate
  3. extractionThe ethyl acetate extract
  4. washwas washed with 75 ml aliquots of saturated sodium bicarbonate, water and brine
  5. dry with materialthen dried over magnesium sulfate
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-20f38895a7c74d7ea9f6c9b0bd5016c0
Source dataset
uspto-grants-1990_09
Patent number
US04959495

Reaction notes

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