Water → HCID 57587039, compound

HRID 1442883Notes

Reaction equation

HRID 1442883 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]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.O>CN(C)C=O.C(Cl)(Cl)Cl.CO>[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]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:11]=1[Br:23])[NH:5][C:6](=[O:8])[CH3:7]

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 12001833HCID 12001833, compound

Product 1

HCID 57587039HCID 57587039, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21584188Chloroform methanolSolvent

Procedure

A solution containing 19.6 mg (0.04 mmol) of (S)-(+)-N-acetyl-2,4,6-tribromo-5-methoxytryptophan methyl ester (4) dissolved in 1.5 mL of N,N-dimethylformamide was charged with 18.0 mg (0.13 mmol) of potassium carbonate and subsequently with 0.09 mL (d =1.44,0.7 mmol) of benzyl bromide. The mixture was stirred at room temperature for 30 minutes. The reaction solution was charged with water and subjected to extraction with an ethyl acetate-methanol (95:5, v/v) mixed solvent. 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. Thin-layer chromatography using silica gel as a carrier and a chloroform-methanol (99:1, v/v) mixed solvent as a developing solvent was performed. A band having an Rf value of 0.18 to 0.29 was extracted with a chloroform-methanol (95:5, v/v) mixed solvent to obtain the substance of interest (8) at a yield of 22.0 mg (96%).

Workup

  1. extractionsubjected to extraction with an ethyl acetate-methanol (95:5
  2. additionv/v) mixed solvent
  3. washThe organic phase was washed with a saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThen, the solvent was distilled off under reduced pressure
  6. customto obtain yellow oil
  7. extractionwas extracted with a chloroform-methanol (95:5
  8. additionv/v) mixed solvent

Sources & evidence

ORD record
ord-277cc23d38514774ad8fbbd448d65630
Source dataset
uspto-grants-2010_02
Patent number
US07659304B2

Reaction notes

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