Water → HCID 57587037, compound

HRID 1442882Notes

Reaction equation

HRID 1442882 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)[C:32]#[CH: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][C:32]#[CH:31])[C:11]=1[Br:23])[NH:5][C:6](=[O:8])[CH3:7]

Participants

6

Reactant 4

HCID 962WaterHCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 12001833HCID 12001833, compound

Product 1

HCID 57587037HCID 57587037, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution containing 23.6 mg (0.04 mmol) of (S)-(+)-N-acetyl-2,4,6-tribromo-5-methoxytryptophan methyl ester (4) dissolved in 2.0 mL of N,N-dimethylformamide was charged with 21.6 mg (0.16 mmol) of potassium carbonate and subsequently with 0.08 mL (d=1.335, 0.9 mmol) of propargyl 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 pink 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 (7) at a yield of 23.9 mg (94%).

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 pink oil
  6. customPurification by column chromatography

Sources & evidence

ORD record
ord-f1272ba5d185428f9ccf613e90079c0d
Source dataset
uspto-grants-2010_02
Patent number
US07659304B2

Reaction notes

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