Methyl iodide → HCID 23378123, compound

HRID 2307822Notes

Reaction equation

HRID 2307822 reaction equation
[C:1]([NH:8][C@H:9]([C:21]([OH:23])=[O:22])[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([OH:20])[CH:18]=2)[NH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].IC.[CH3:26]COC(C)=O>CN(C=O)C>[CH3:26][O:22][C:21](=[O:23])[C@@H:9]([NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:7])[CH3:6])=[O:2])[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([OH:20])[CH:18]=2)[NH:13][CH:12]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11404411HCID 11404411, compound

Product 1

HCID 23378123HCID 23378123, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of BOC-5-hydroxy-tryptophan (5.9 g, 18.4 mmol) and iodomethane (3.43 mL) in DMF (80 mL) was added powered KHCO3 (3.68 g). The reaction mixture was stirred at rt for 4 hours. EtOAc (500 mL) was added and the mixture was washed with brine (500 mL) and water (500 mL). The organic phase was concentrated and the residual oil was triturated with CH2Cl2 (20 mL). The formed white solid was collected by filtration, washed with CH2Cl2 (20 mL) and dried to give the desired product (4.48 g, 73%). MS (DCI) m/z 335 (M+1)+.

Workup

  1. washthe mixture was washed with brine (500 mL) and water (500 mL)
  2. concentrationThe organic phase was concentrated
  3. customthe residual oil was triturated with CH2Cl2 (20 mL)
  4. filtrationThe formed white solid was collected by filtration
  5. washwashed with CH2Cl2 (20 mL)
  6. customdried

Sources & evidence

ORD record
ord-3f4f017e7c2d4fd88bffa01e43c4c52c
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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