Methyl iodide → HCID 86655460, compound

HRID 1746502Notes

Reaction equation

HRID 1746502 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[C:7]([O:11][C:12]([NH:14][C@H:15]([C:28]([OH:30])=[O:29])[CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]([CH:26]=[O:27])[CH:18]=1)=[O:13])([CH3:10])([CH3:9])[CH3:8].IC>CN(C=O)C>[C:7]([O:11][C:12]([NH:14][C@H:15]([C:28]([O:30][CH3:1])=[O:29])[CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]([CH:26]=[O:27])[CH:18]=1)=[O:13])([CH3:10])([CH3:8])[CH3:9]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 7017963Boc-Trp(For)-OH

Product 1

HCID 86655460HCID 86655460, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To DMF (50 mL) suspension of potassium carbonate (6.2 g) was added dropwise DMF (70 mL) solution of Nα-tert-butoxycarbonyl-1-formyl-L-tryptophan (10.0 g) at 0° C., and the mixture was stirred for 1 hour at room temperature. Next, DMF (25 mL) solution of iodomethane (2.8 mL) was added dropwise at 0° C., and the mixture was stirred for 20 hours at room temperature. The reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and thereafter the residue obtained by distilling off the solvent under a reduced pressure was purified with silica gel column chromatography (BZ-127ZH, n-hexane:ethyl acetate=7:3), to give the captioned compound (9.0 g, 86%) as crystals.

Workup

  1. stirringthe mixture was stirred for 20 hours at room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customthe residue obtained
  5. distillationby distilling off the solvent under a reduced pressure
  6. customwas purified with silica gel column chromatography (BZ-127ZH, n-hexane:ethyl acetate=7:3)

Sources & evidence

ORD record
ord-81431132166349b59c5678f897b8edc7
Source dataset
uspto-grants-2015_10
Patent number
US09150510B2

Reaction notes

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