Imidazole → N-Boc-5-Iodo-L-norvaline tert-butyl ester

HRID 276732Notes

Reaction equation

HRID 276732 reaction equation
O[CH2:2][CH2:3][CH2:4][C@H:5]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:45]I>C(Cl)Cl.CO>[I:45][CH2:2][CH2:3][CH2:4][C@H:5]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 10062769(S)-tert-butyl 2-((tert-butoxycarbonyl)amino)-5-hydroxypentanoate

Product 1

HCID 15479354N-Boc-5-Iodo-L-norvaline tert-butyl ester

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of t-butyl (S)-5-hydroxy-2-(t-butoxycarbonylamino)-pentanoate (5.79 g, 20.0 mmol), triphenylphosphine (8.13 g, 31.0 mmol) and imidazole (2.04 g, 30.0 mmol) in CH2Cl2 (200 mL) at room temperature is added iodine (6.35 g, 25.0 mmol), portionwise, over 30 minutes. The mixture is then stirred 16 hours at room temperature. Methanol (20 mL) is added to the solution, which is then stirred an additional 1 hour. Solvent is evaporated, and the residue is purified by chromatography (silica, 33% EtOAc/hexane) to yield t-butyl (S)-5-iodo-2-(t-butoxycarbonylamino)-pentanoate as a clear oil.

Workup

  1. stirringis then stirred an additional 1 hour
  2. customSolvent is evaporated
  3. customthe residue is purified by chromatography (silica, 33% EtOAc/hexane)

Sources & evidence

ORD record
ord-7c6289faa39441d3824ed62cc75a584e
Source dataset
uspto-grants-2002_03
Patent number
US06353017B1

Reaction notes

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