Benzyl Bromide → HCID 88125651, compound

HRID 1079370Notes

Reaction equation

HRID 1079370 reaction equation
[CH:1]([O:14][C:15]1[C:16](=[O:43])[N:17]=[C:18]([S:22][CH:23]2[C:28]([CH3:29])=[C:27]([C:30]([C:32]([CH3:35])([CH3:34])[CH3:33])=[O:31])[N:26]3[C:36](=[O:40])[C@H:37]([O:38][CH3:39])[C@H:25]3[S:24]2(=[O:42])=[O:41])[N:19]([CH3:21])[N:20]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:51](Br)[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1>C(#N)C.ClCCl>[CH:1]([O:14][C:15]1[C:16](=[O:43])[N:17]=[C:18]([S:22][C:23]2([CH2:51][C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[C:28]([CH3:29])=[C:27]([C:30]([C:32]([CH3:35])([CH3:34])[CH3:33])=[O:31])[N:26]3[C:36](=[O:40])[C@H:37]([O:38][CH3:39])[C@H:25]3[S:24]2(=[O:41])=[O:42])[N:19]([CH3:21])[N:20]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 88125531HCID 88125531, compound

Product 1

HCID 88125651HCID 88125651, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(6-benzhydryloxy-2-methyl-5-oxo-2,5-dihydro-1,2,4-triazin-3-yl)thio-4-tert-butylcarbonyl-7α-methoxy-3-methyl-3-cephem 1,1-dioxide (300 mg) in acetonitrile (5 ml) was treated at room temperature with triethylamine (0.067 ml) and benzyl bromide (0.172 ml). After 4 hr, the reaction mixture was diluted with dichloromethane, washed with brine and dried over Na2SO4. The solvent was then removed and the residue purified by flash chromatography, thereby obtaining the title compound as a white solid (180 mg).

Workup

  1. washwashed with brine
  2. dry with materialdried over Na2SO4
  3. customThe solvent was then removed
  4. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-5a8eeefce4684d6ba458d1f01d26c98d
Source dataset
uspto-grants-1996_12
Patent number
US05580865

Reaction notes

Loading…