Methyl iodide → HCID 13821420, compound

HRID 2070133Notes

Reaction equation

HRID 2070133 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:20]([OH:22])=[O:21])[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:23]C(C)([O-])C.[K+].IC>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([CH3:23])[CH:12]=1)[C:20]([OH:22])=[O:21])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 111050N-((tert-Butoxy)carbonyl)-D-tryptophanHCID 23665647Potassium tert-butoxide

Product 1

HCID 13821420HCID 13821420, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

N-tert-Butoxycarbonyl-D-tryptophan (3.0 g) was dissolved in N,N-dimethylformaldehyde (30 mL) under argon, and potassium tert-butoxide (as 12% tetrahydrofuran solution) (17.7 g) was added dropwise thereto under cooling on ice, followed by stirring for 15 minutes. A solution of iodomethane (2.1 g) in N,N-dimethylformaldehyde (3.0 mL) was added to the mixture, and stirring was performed for 10 minutes. The resultant mixture was partitioned between 30% aqueous citric acid solution and ethyl acetate, and the organic layer was sequentially washed with 30% aqueous citric acid solution and saturated aqueous sodium chloride solution, followed by drying over sodium sulfate. The solvent was evaporated under reduced pressure, and diisopropyl ether was added to the thus-recovered residue. The precipitates were recovered through filtration, washed with diisopropyl ether, and dried under reduced pressure, whereby the title compound (1.89 g) was yielded.

Workup

  1. temperatureunder cooling on ice
  2. stirringstirring
  3. waitwas performed for 10 minutes
  4. customThe resultant mixture was partitioned between 30% aqueous citric acid solution and ethyl acetate
  5. washthe organic layer was sequentially washed with 30% aqueous citric acid solution and saturated aqueous sodium chloride solution
  6. dry with materialby drying over sodium sulfate
  7. customThe solvent was evaporated under reduced pressure, and diisopropyl ether
  8. additionwas added to the thus-recovered residue
  9. filtrationThe precipitates were recovered through filtration
  10. washwashed with diisopropyl ether
  11. dry with materialdried under reduced pressure, whereby the title compound (1.89 g)
  12. customwas yielded

Sources & evidence

ORD record
ord-be8261d95efd469fb4697f46b6367b07
Source dataset
uspto-grants-2012_10
Patent number
US08299255B2

Reaction notes

Loading…