Triethylamine → HCID 131719736, compound

HRID 1079372Notes

Reaction equation

HRID 1079372 reaction equation
[C:1]([C:5]([C:7]1[N:12]2[C:13](=[S:17])[C@H:14]([O:15][CH3:16])[C@H:11]2[S:10](=[O:19])(=[O:18])[CH:9]([C:20]2[N:24]([CH3:25])[N:23]=[N:22][N:21]=2)[C:8]=1[CH3:26])=[O:6])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH:34]([O:47][C:48](=[O:57])[C:49]1[CH:54]=[CH:53][C:52]([CH2:55]Br)=[CH:51][CH:50]=1)([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>CS(C)=O.ClCCl>[CH:34]([O:47][C:48]([C:49]1[CH:50]=[CH:51][C:52]([CH2:55][C:9]2([C:20]3[N:24]([CH3:25])[N:23]=[N:22][N:21]=3)[C:8]([CH3:26])=[C:7]([C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[O:6])[N:12]3[C:13](=[S:17])[C@H:14]([O:15][CH3:16])[C@H:11]3[S:10]2(=[O:19])=[O:18])=[CH:53][CH:54]=1)=[O:57])([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 23366658HCID 23366658, compoundHCID 131719733HCID 131719733, compound

Product 1

HCID 131719736HCID 131719736, compoundYield 28.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-tert-butylcarbonyl-7α-methoxy-3-methyl-2-(1-methyl-1,2,3,4-tetrazol-5-yl)thio-3-cephem 1,1-dioxide (500 mg) in dimethyl sulphoxide (4 ml) was treated at room temperature with triethylamine (0.185 ml) and benzhydryl-4-bromomethylbenzoate (1.4 g). The solution was stirred for 1 hr, diluted with dichloromethane, washed with brine and eventually dried over Na2SO4. Removal of the solvent left a crude residue which afforded the title compound as a yellowish solid (250 mg) after flash chromatography.

Workup

  1. washwashed with brine
  2. dry with materialeventually dried over Na2SO4
  3. customRemoval of the solvent
  4. waitleft a crude residue which

Sources & evidence

ORD record
ord-8fa1bd0b558d400a99f9617961a9a5ae
Source dataset
uspto-grants-1996_12
Patent number
US05580865

Reaction notes

Loading…