Triethylamine → HCID 70080899, compound

HRID 1081565Notes

Reaction equation

HRID 1081565 reaction equation
[C:1]([C:5]([C:7]1[N:12]2[C:13](=[O:17])[C@H:14]([O:15][CH3:16])[C@H:11]2[S:10](=[O:19])(=[O:18])[CH2:9][C:8]=1[CH2:20][S:21][C:22]1[N:26]([CH3:27])[N:25]=[N:24][N:23]=1)=[O:6])([CH3:4])([CH3:3])[CH3:2].[Br:28]N1C(=O)CCC1=O.C(N(CC)CC)C>ClCCl>[Br:28][CH:9]1[C:8]([CH2:20][S:21][C:22]2[N:26]([CH3:27])[N:25]=[N:24][N:23]=2)=[C:7]([C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[O:6])[N:12]2[C:13](=[O:17])[C@H:14]([O:15][CH3:16])[C@H:11]2[S:10]1(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67184N-bromobutanimideHCID 15178146HCID 15178146, compound

Product 1

HCID 70080899HCID 70080899, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-tert-butylcarbonyl-7α-methoxy-3-(1-methyl-1,2,3,4-tetrazol-5-yl)thiomethyl-3-cephem 1,1 dioxide (350 mg) in dichloromethane (30 ml), N-bromosuccinimide (200 mg) and triethylamine (0.13 ml) were added sequentially. The mixture was stirred for 15 min at room temperature. Following dilution with dichloromethane, the organic phase was sequentially washed with 4% aqueous NaHSO3, saturated NaHCO3 and water. After drying over Na2SO4 and removal of the solvent, the residue was purified by flash chromatography (eluting with hexane-EtOAc mixtures) affording 2-bromo-4-tert-butylcarbonyl-7α-methoxy-3-(1-methyl-1,2,3,4-tetrazol-5-yl) thiomethyl-3-cephem 1,1-dioxide as a waxy solid (200 mg), IR (KBr) νmax 1800, 1700 cm-1. A portion of this material (180 mg) was dissolved in acetonitrile (10 ml) and treated with silver benzoate (95 mg). The mixture was stirred for 30 min at room temperature, then filtered and rotoevaporated. Following flash chromatography (eluting with gradient of EtOAc in hexane) the title product was obtained as a light yellow solid (80 mg).

Workup

  1. washthe organic phase was sequentially washed with 4% aqueous NaHSO3, saturated NaHCO3 and water
  2. dry with materialAfter drying over Na2SO4 and removal of the solvent
  3. customthe residue was purified by flash chromatography (eluting with hexane-EtOAc mixtures)

Sources & evidence

ORD record
ord-88158f354ba346ceb798ba4dee34326a
Source dataset
uspto-grants-1996_12
Patent number
US05587373

Reaction notes

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