Methyl iodide → HCID 13821420, compound

HRID 2256839Notes

Reaction equation

HRID 2256839 reaction equation
[NH:1]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@@H:2]([C:13]([OH:15])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[CH3:23]C(C)([O-])C.[K+].CI>CN(C=O)C>[NH:1]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@@H:2]([C:13]([OH:15])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([CH3:23])[CH:5]=1

Participants

5

Reactant 3

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

Product 1

HCID 13821420HCID 13821420, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Boc-D-Trp-OH (15.0 g) in DMF (150 ml) were added potassium tert-butoxide (13.8 g) and methyl iodide (10.5 g) under ice-cooling. After stirring under ice-cooling for 30 minutes and at room temperature for 15 minutes, the reaction mixture was poured into ice-cooled 0.24 NHCl, followed by extraction with ethyl acetate. The extract was washed with 5% NaHSO3 and saturated aqueous sodium chloride. Removal of the solvent gave a residue, which was crystallized from diisopropyl ether to afford Boc-D-Trp(CH3)-OH (9.18 g).

Workup

  1. temperaturecooling
  2. additionthe reaction mixture was poured into ice-
  3. temperaturecooled 0.24 NHCl
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe extract was washed with 5% NaHSO3 and saturated aqueous sodium chloride
  6. customRemoval of the solvent
  7. customgave a residue, which
  8. customwas crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-8032dfaf30d343f2ab21d56cf9bfde73
Source dataset
uspto-grants-1997_08
Patent number
US05656604

Reaction notes

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