Imidazole → HCID 68575959, compound

HRID 1797268Notes

Reaction equation

HRID 1797268 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:20]I.N1C=CN=C1.[CH2:27]([O:34][C:35](=[O:49])[NH:36][C@H:37]([CH2:40][NH:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:38]O)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(Cl)Cl>[CH2:27]([O:34][C:35](=[O:49])[NH:36][C@H:37]([CH2:40][NH:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:38][I:20])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 51340611HCID 51340611, compound

Product 1

HCID 68575959HCID 68575959, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triphenylphosphine bound to cross-linked polystyrene resin (0.82 g, 3 mmol/g, 2.47 mmol) is suspended in dry DCM (10 ml) at ambient temperature under a nitrogen atmosphere. Iodine (0.62 g, 2.47 mmol) is added and the reaction mixture stirred for 15 minutes. Imidazole (0.167 g, 2.47 mmol) is then added and the reaction mixture is stirred for a further 15 minutes. A solution of [(R)-1-(tert-butoxycarbonylamino-methyl)-2-hydroxy-ethyl]-carbamic acid benzyl ester (0.401 g, 1.23 mmol) in dry dichloromethane (5 ml) is added and the reaction mixture is stirred at reflux for 1.5 hour. The polymer is removed by filtration, and the filtrate is first washed with aqueous 5% sodium thiosulphate solution and then water. The organic phase is dried over MgSO4 and evaporated to yield [(R)-1-(tert-butoxycarbonylamino-methyl)-2-iodo-ethyl]-carbamic acid benzyl ester. [MH]+ 435.0.

Workup

  1. stirringthe reaction mixture is stirred for a further 15 minutes
  2. stirringthe reaction mixture is stirred
  3. temperatureat reflux for 1.5 hour
  4. customThe polymer is removed by filtration
  5. washthe filtrate is first washed with aqueous 5% sodium thiosulphate solution
  6. dry with materialThe organic phase is dried over MgSO4
  7. customevaporated

Sources & evidence

ORD record
ord-2fd16dafc38149aa87c4f2a2d212c7b3
Source dataset
uspto-grants-2006_04
Patent number
US07034042B2

Reaction notes

Loading…