Triethylamine → (2R)-N-benzyl-N-benzyloxycarbonylmethyl-2-(tert-butoxycarbonylamino)-3-(N-formyl-1H-indol-3-yl)propanamide

To a mixture of N2 -(tert-butoxycarbonyl)-N1 -formyl-D-tryptophan (3.99 g) and N-benzyl glycin benzyl ester hydrochloride (3.50 g) in dichloromethane (70 ml) was added triethylamine (5.85 ml) under nitrogen atmosphere. To the mixture was added 2-chloro-1-methylpyridinium iodide (3.67 g) at room temperature, and the resulting mixture was stirred for 2 hours. After the reaction was completed, dichloromethane (30 ml) and water (30 ml) were added. The organic layer was separated, washed with 0.5N hydrochloric acid (10 ml), water (10 ml), aqueous sodium bicarbonate solution (10 ml) and brine (20 ml) successively and dried over magnesium sulfate. After evaporation of the solvent, the residue was purified on a silica gel column (140 g) eluting with a mixture of toluene and ethyl acetate (4:1) to give (2R) -N-benzyl-N-benzyloxycarbonylmethyl-2- (tert-butoxycarbonylamino)-3-(N-formyl-1H-indol-3-yl)propanamide (6.41 g) as an oil.

1. customThe organic layer was separated
2. washwashed with 0.5N hydrochloric acid (10 ml), water (10 ml), aqueous sodium bicarbonate solution (10 ml) and brine (20 ml) successively
3. dry with materialdried over magnesium sulfate
4. customAfter evaporation of the solvent
5. customthe residue was purified on a silica gel column (140 g)
6. washeluting with a mixture of toluene and ethyl acetate (4:1)

ORD record

ord-183611ff0cb04b9db5b5feb61da64df3

Source dataset

uspto-grants-1999_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05883098