Water → HCID 57587036, compound

HRID 1442881Notes

Reaction equation

HRID 1442881 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C@H:4]([CH2:9][C:10]1[C:18]2[C:13](=[CH:14][C:15]([Br:22])=[C:16]([O:20][CH3:21])[C:17]=2[Br:19])[NH:12][C:11]=1[Br:23])[NH:5][C:6](=[O:8])[CH3:7].C(=O)([O-])[O-].[K+].[K+].[CH2:31](Br)[CH:32]=[CH2:33].O>CN(C)C=O>[CH3:1][O:2][C:3](=[O:24])[C@H:4]([CH2:9][C:10]1[C:18]2[C:13](=[CH:14][C:15]([Br:22])=[C:16]([O:20][CH3:21])[C:17]=2[Br:19])[N:12]([CH2:33][CH:32]=[CH2:31])[C:11]=1[Br:23])[NH:5][C:6](=[O:8])[CH3:7]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 12001833HCID 12001833, compound

Product 1

HCID 57587036HCID 57587036, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution containing 39.8 mg (0.08 mmol) of (S)-(+)-N-acetyl-2,4,6-tribromo-5-methoxytryptophan methyl ester (4) dissolved in 2.5 mL of N,N-dimethylformamide was charged with 36.5 mg (0.26 mmol) of potassium carbonate and subsequently with 0.13 mL (d=1.398, 1.51 mmol) of allyl bromide. The mixture was stirred at room temperature for 30 minutes. The reaction solution was charged with water and subjected to extraction with ethyl acetate. The organic phase was washed with a saturated saline and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure to obtain yellow oil. Purification by column chromatography using silica gel as a carrier and chloroform as an elution solvent was performed to obtain the substance of interest (6) at a yield of 42.4 mg (99%).

Workup

  1. extractionsubjected to extraction with ethyl acetate
  2. washThe organic phase was washed with a saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThen, the solvent was distilled off under reduced pressure
  5. customto obtain yellow oil
  6. customPurification by column chromatography

Sources & evidence

ORD record
ord-9e0e073931554504b0a17f44d8966ca7
Source dataset
uspto-grants-2010_02
Patent number
US07659304B2

Reaction notes

Loading…