Sodium Iodide → HCID 23387582, compound

HRID 1790732Notes

Reaction equation

HRID 1790732 reaction equation
Cl[CH2:2][O:3][C:4](=[O:18])[C@H:5]([C@H:14]([CH2:16][CH3:17])[CH3:15])[NH:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[I-:19].[Na+]>C(#N)C>[I:19][CH2:2][O:3][C:4](=[O:18])[C@H:5]([C@H:14]([CH2:16][CH3:17])[CH3:15])[NH:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 10401400HCID 10401400, compound

Product 1

HCID 23387582HCID 23387582, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of N-BOC-L-isoleucine chloromethyl ester (19.6 g, 70 mmol) in acetonitrile (300 mL), was added sodium iodide (31.5 g, 210 mmol). The solution was stirred for 4 h at 60° C. The resulting suspension was filtered and the filtrate was evaporated. The residue was dissolved in CH2Cl2 and washed with aqueous sodium thiosulfate (0.1 M). The organic phase was dried (Na2SO4) and concentrated under reduced pressure. The crude product was column chromatographed (silica gel, 2% MeOH in CH2Cl2), to give 22.6 g of N-BOC-L-isoleucine iodomethyl ester.

Workup

  1. filtrationThe resulting suspension was filtered
  2. customthe filtrate was evaporated
  3. dissolutionThe residue was dissolved in CH2Cl2
  4. washwashed with aqueous sodium thiosulfate (0.1 M)
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customchromatographed (silica gel, 2% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-74abcbab50d444e0b4279f6817692f42
Source dataset
uspto-grants-2006_07
Patent number
US07071173B2

Reaction notes

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