Imidazole → (R)-2-tert-butoxycarbonylamino-3-iodopropionic acid tert-butyl ester

HRID 660633Notes

Reaction equation

HRID 660633 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[I:20]I.N1C=CN=C1.[C:27]([O:31][C:32](=[O:44])[C@@H:33]([NH:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:34]O)([CH3:30])([CH3:29])[CH3:28]>C(Cl)Cl>[C:27]([O:31][C:32](=[O:44])[C@@H:33]([NH:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:34][I:20])([CH3:30])([CH3:29])[CH3:28]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 7019054Boc-Ser-Otbu

Product 1

HCID 54762716(R)-2-tert-butoxycarbonylamino-3-iodopropionic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of PPh3-resin (5 g, 6.5 mmol) in methylene chloride (50 mL) at 0° C. is added iodine (1.65 g, 6.5 mmol) and imidazole (0.485 g, 7.12 mmol) then stirring is continued at 0° C. for 45 min. To this is added (S)-2-tert-butoxycarbonylamino-3-hydroxypropionic acid tert-butyl ester (0.81 g, 3.1 mmol) and the suspension is refluxed for 45 min. The suspension is filtered and the organic layer is washed with a saturated sodium bisulfite solution, water and brine, and dried over sodium sulfate. The solvent is removed under reduced pressure to afford the title compound as a white solid.

Workup

  1. temperaturethe suspension is refluxed for 45 min
  2. filtrationThe suspension is filtered
  3. washthe organic layer is washed with a saturated sodium bisulfite solution, water and brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-f7252fc2479c415ea572dc52b70cfa97
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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