Imidazole → ((s)-3-Iodo-1-methoxymethyl-propyl)-carbamic acid tert-butyl ester

HRID 1182122Notes

Reaction equation

HRID 1182122 reaction equation
[I:1]I.N1C=CN=C1.[C:8]([O:12][C:13](=[O:22])[NH:14][C@H:15]([CH2:19][O:20][CH3:21])[CH2:16][CH2:17]O)([CH3:11])([CH3:10])[CH3:9]>ClCCl>[C:8]([O:12][C:13](=[O:22])[NH:14][C@H:15]([CH2:19][O:20][CH3:21])[CH2:16][CH2:17][I:1])([CH3:11])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 807IodineHCID 53259998tert-Butyl (S)-(4-hydroxy-1-methoxybutan-2-yl)carbamate

Product 1

HCID 86600851((s)-3-Iodo-1-methoxymethyl-propyl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of polystyrene resin-bound triphenylphosphine (18.645 g, 3 mmol/g) in dry dichloromethane (250 ml) is treated with iodine (12.5 g, 49.22 mmol) and stirred for 15 minutes under argon. Imidazole (3.87 g, 55.94 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)-3-Hydroxy-1-methoxymethyl-propyl)-carbamic acid tert-butyl ester (4.9 g, 22.37 mmol) in dichloromethane (30 ml), and refluxed for 1.5 hours under argon. The resin is removed by filtration through a celite pad, washing with dichloromethane. The filtrate is washed with 5% aqueous sodium thiosulphate solution and water, dried over MgSO4 and evaporated to afford ((S)-3-Iodo-1-methoxymethyl-propyl)-carbamic acid tert-butyl ester as a crude oil. [M-BOC] 230.06.

Workup

  1. stirringthe reaction mixture stirred at room temperature for a further 15 minutes
  2. temperaturerefluxed for 1.5 hours under argon
  3. customThe resin is removed by filtration through a celite pad
  4. washwashing with dichloromethane
  5. washThe filtrate is washed with 5% aqueous sodium thiosulphate solution and water
  6. dry with materialdried over MgSO4
  7. customevaporated

Sources & evidence

ORD record
ord-75e5c7ae8e85446c9f4e6571ebc35a00
Source dataset
uspto-grants-2007_10
Patent number
US07288537B2

Reaction notes

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