Triethylamine → Tri-n-propylsilyl 7-benzamido-2-bromo-3-bromomethyl-3-cephem-4-carboxylate-1-oxide

HRID 67964Notes

Reaction equation

HRID 67964 reaction equation
[CH2:1]([Si:4]([CH2:9][CH2:10][CH3:11])([CH2:6][CH2:7][CH3:8])Cl)[CH2:2][CH3:3].[C:12]([NH:20][CH:21]1[C:35](=[O:36])[N:23]2[C:24]([C:32]([OH:34])=[O:33])=[C:25]([CH2:30][Br:31])[CH:26]([Br:29])[S:27](=[O:28])[C@H:22]12)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C>ClCCCl>[C:12]([NH:20][CH:21]1[C:35](=[O:36])[N:23]2[C:24]([C:32]([O:34][Si:4]([CH2:9][CH2:10][CH3:11])([CH2:6][CH2:7][CH3:8])[CH2:1][CH2:2][CH3:3])=[O:33])=[C:25]([CH2:30][Br:31])[CH:26]([Br:29])[S:27](=[O:28])[C@H:22]12)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70445ChlorotripropylsilaneHCID 70463170HCID 70463170, compound

Product 1

HCID 70464922Tri-n-propylsilyl 7-benzamido-2-bromo-3-bromomethyl-3-cephem-4-carboxylate-1-oxideYield 51.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

123 mg of tri-n-propylchlorosilane were added to a suspension of 312 mg of 7-benzamido-2-bromo-3-bromomethyl-3-cephem-4-carboxylic acid-1-oxide (prepared by the process of Step D of Example 1) in 25 ml of 1,2-dichloroethane under a nitrogen atmosphere and then a solution of 64 mg of triethyl-amine in 4 ml of 1,2-dichloroethane was dropwise added over 15 minutes under cooling in an ice-bath. The clear, slightly yellow colored solution was stirred for two hours at room temperature and after removal of the solvent under vacuo, 7 ml of diethyl ether was added. The obtained suspension was centrifuged and the clear liquid layer was separated and evaporated to dryness under vacuo. The residue was kept at a pressure of 0.5 mm of mercury for half an hour to obtain 210 mg of tri-n-propylsilyl 7-benzamido-2-bromo-3-bromomethyl-3-cephem-4-carboxylate-1-oxide having the following characteristics:

Workup

  1. temperatureunder cooling in an ice-bath
  2. customafter removal of the solvent under vacuo, 7 ml of diethyl ether
  3. additionwas added
  4. customthe clear liquid layer was separated
  5. customevaporated to dryness under vacuo
  6. waitThe residue was kept at a pressure of 0.5 mm of mercury for half an hour

Sources & evidence

ORD record
ord-0274a580b3a24b3f8edf1ec0ecff52b0
Source dataset
uspto-grants-1982_08
Patent number
US04347358

Reaction notes

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