Iodoethane → HCID 70248552, compound

HRID 1533286Notes

Reaction equation

HRID 1533286 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([C@H:10]([C@H:28]([OH:33])[CH2:29][CH2:30][CH2:31][CH3:32])[C:11]([NH:13][C@H:14]([C:25]([OH:27])=[O:26])[CH2:15][C:16]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[NH:18][CH:17]=3)=[O:12])=[CH:4][C:3]=2[O:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:40](I)[CH3:41]>CN(C)C=O.C(OCC)(=O)C>[CH2:40]([O:26][C:25](=[O:27])[C@H:14]([CH2:15][C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[NH:18][CH:17]=1)[NH:13][C:11](=[O:12])[C@H:10]([C:5]1[CH:6]=[CH:7][C:8]2[O:9][CH2:1][O:2][C:3]=2[CH:4]=1)[C@H:28]([OH:33])[CH2:29][CH2:30][CH2:31][CH3:32])[CH3:41]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 20640756HCID 20640756, compound

Product 1

HCID 70248552HCID 70248552, compoundYield 81.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Nα-[(2R,3R)-2-(3,4-methylenedioxyphenyl)-3-hydroxyheptanoyl]-L-tryptophan (300 mg) in N,N-dimethylformamide (10 ml) were added potassium carbonate (69 mg) and ethyl iodide (155 mg) and the mixture was stirred at ambient temperature for 3 hours. The mixture was diluted with ethyl acetate (20 ml) and the solution was washed with 0.5N hydrochloric acid (20 ml×2), saturated sodium bicarbonate aqueous solution (20 ml×2) and brine (20 ml) successively and the organic layer was dried over magnesium sulfate. The solution was concentrated in vacuo and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give N [(2R,3R)-2-(3,4-methylenedioxyphenyl)-3-hydroxyheptanoyl]-L-tryptophan ethyl ester as an amorphous powder (260 mg).

Workup

  1. washthe solution was washed with 0.5N hydrochloric acid (20 ml×2), saturated sodium bicarbonate aqueous solution (20 ml×2) and brine (20 ml) successively
  2. dry with materialthe organic layer was dried over magnesium sulfate
  3. concentrationThe solution was concentrated in vacuo
  4. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-e56256cb1ccf42a9af6ff7a2ba6df99b
Source dataset
uspto-grants-2001_03
Patent number
US06207686B1

Reaction notes

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