Sodium Iodide → N-Phthalimidomethyl-L-leucyl-L-phenylalanine N-methylamide

HRID 1872494Notes

Reaction equation

HRID 1872494 reaction equation
[CH3:1][NH:2][C:3](=[O:21])[C@H:4]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[NH:5][C:6](=[O:13])[C@H:7]([CH2:9][CH:10]([CH3:12])[CH3:11])[NH2:8].Br[CH2:23][N:24]1[C:28](=[O:29])[C:27]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]2[C:25]1=[O:34].[I-].[Na+].C(=O)(O)[O-].[Na+]>ClCCl>[CH3:1][NH:2][C:3](=[O:21])[C@H:4]([CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[NH:5][C:6](=[O:13])[C@H:7]([CH2:9][CH:10]([CH3:12])[CH3:11])[NH:8][CH2:23][N:24]1[C:25](=[O:34])[C:26]2=[CH:33][CH:32]=[CH:31][CH:30]=[C:27]2[C:28]1=[O:29]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 792441H-Isoindole-1,3(2H)-dione, 2-(bromomethyl)-HCID 516892Sodium BicarbonateHCID 18394511L-Leucyl-L-phenylalanine methylamide

Product 1

HCID 70138784N-Phthalimidomethyl-L-leucyl-L-phenylalanine N-methylamideYield 36.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of L-leucyl-L-phenylalanine N-methylamide (1.3 g) in dichloromethane (13 ml) was treated with N-bromomethylphthalimide (1.17 g) and sodium iodide (0.06 g). The resulting yellow solution was stirred at room temperature for 16 h. The solution was treated with saturated sodium bicarbonate solution (ca. 8 ml) and extracted with dichloromethane. The crude, organic extracts were preadsorbed onto silica gel and purified by flash silica chromatography, eluting with ethyl acetate/heptane (5:1), to furnish the title compound as a white solid (0.74 g).

Workup

  1. extractionextracted with dichloromethane
  2. custompurified by flash silica chromatography
  3. washeluting with ethyl acetate/heptane (5:1)

Sources & evidence

ORD record
ord-7ec84b4ed8c44d7ba8f58f3b175f846f
Source dataset
uspto-grants-2000_08
Patent number
US06110896

Reaction notes

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