Imidazole → HCID 131726651, compound

HRID 1182096Notes

Reaction equation

HRID 1182096 reaction equation
[I:1]I.N1C=CN=C1.[C:8]([O:12][C:13](=[O:38])[NH:14][C@H:15]([C:19]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[O:20][SiH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:16][CH2:17]O)([CH3:11])([CH3:10])[CH3:9]>ClCCl>[C:8]([O:12][C:13](=[O:38])[NH:14][C@H:15]([C:19]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[O:20][SiH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:16][CH2:17][I:1])([CH3:11])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 807IodineHCID 131726652HCID 131726652, compound

Product 1

HCID 131726651HCID 131726651, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of polystyrene resin-bound triphenylphosphine (2.33 g, 3 mmol/g in dry dichloromethane (25 ml) is treated with iodine (1.56 g, 6.16 mmol) and stirred for 15 minutes under argon. Imidazole (0.477 g, 7.0 mmol) is added and the reaction mixture stirred at room temperature for a further 15 minutes. The reaction mixture is then treated with a solution of [(S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxy-propyl]carbamic acid tert-butyl ester (1.24 g, 2.8 mmol) in dichloromethane (5 ml). The reaction mixture is refluxed for 2 hours under argon, then filtered through a Celite™ filter pad, washing with dichloromethane. The filtrate is washed with 5% aqueous sodium thiosulphate solution and water, dried over MgSO4 and evaporated. The crude product is purified by flash silica chromatography (elution with 1:99 methanol/dichloromethane) to afford [(S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-3-iodo-propyl]-carbamic acid tert-butyl ester. [M-BOC] 453.9.

Workup

  1. stirringthe reaction mixture stirred at room temperature for a further 15 minutes
  2. temperatureThe reaction mixture is refluxed for 2 hours under argon
  3. filtrationfiltered through a Celite™
  4. filtrationfilter pad
  5. washwashing with dichloromethane
  6. washThe filtrate is washed with 5% aqueous sodium thiosulphate solution and water
  7. dry with materialdried over MgSO4
  8. customevaporated
  9. customThe crude product is purified by flash silica chromatography (elution with 1:99 methanol/dichloromethane)

Sources & evidence

ORD record
ord-682f7d1ce4e64c9cad1e83bf104d0f0c
Source dataset
uspto-grants-2007_10
Patent number
US07288537B2

Reaction notes

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