Methyl 4-iodobutanoate → N-(Methoxycarbonyl)propyl-L-leucyl-L-phenylalanine N-methylamide

HRID 1872493Notes

Reaction equation

HRID 1872493 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].I[CH2:23][CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27]>C(O)C>[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][CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27]

Participants

4

Reactant 2

HCID 547991Methyl 4-iodobutanoateHCID 18394511L-Leucyl-L-phenylalanine methylamide

Product 1

HCID 53871324N-(Methoxycarbonyl)propyl-L-leucyl-L-phenylalanine N-methylamideYield 26.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
45 °C

Procedure

A solution of L-leucyl-L-phenylalanine N-methylamide (1.19 g) in ethanol (24 ml) was treated with methyl 4-iodobutyrate (0.93 g); the resulting colourless solution was heated to 45° C. over 16 h. The crude product was purified by flash silica chromatography, eluting with ethyl acetate/heptane (1:1 to 5:1), to furnish the title compound as an off-white solid (0.42 g).

Workup

  1. customThe crude product was purified by flash silica chromatography
  2. washeluting with ethyl acetate/heptane (1:1 to 5:1)

Sources & evidence

ORD record
ord-9761ce3e4eeb48c48908901f9a282766
Source dataset
uspto-grants-2000_08
Patent number
US06110896

Reaction notes

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