Water → HCID 131720744, compound
Reaction equation
[C:1]([O:5]C(N[C@H](C(O)=O)CC1C2C(=CC=CC=2)NC=1)=O)([CH3:4])([CH3:3])[CH3:2].[CH3:23][NH:24][CH:25](N)[CH3:26].O[N:29]1[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=2[N:31]=N1.[OH2:38].CCN=C=N[CH2:44][CH2:45][CH2:46]N(C)C.[CH3:50][N:51]([CH:53]=[O:54])[CH3:52]>>[CH3:23][NH:24][CH2:25][CH2:26][NH:29][C:33](=[O:38])[C@H:32]([CH2:37][C:36]1[C:35]2[C:52](=[CH:44][CH:45]=[CH:46][CH:34]=2)[N:51]([C:53]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:54])[CH:50]=1)[NH2:31]Participants
Procedure
To N-t-butoxycarbonyltryptophan (3 mmol, 914 mg) and N-methylethanediamine (3.6 mmol, 0.27 g, 0.32 mL) in dry DMF (15 mL) were added 1-hydroxybenzotriazole.H2O (3 mmol, 459 mg) and EDCI (4.5 mmol, 863 mg). The mixture was stirred at room temperature overnight under argon and excess of the solvent (DMF) was removed under high vacuum at 35° C. The residue was dissolved in ethyl acetate (40 mL) and the adduct was extracted into 1N HCl (3×25 mL). The combined aqueous extract was basified with solid K2CO3 and extracted with ethyl acetate (3×25 mL). The combined organic extract was washed with brine (30 mL) and dried (MgSO4). Evaporation to dryness yielded 920 mg (85%) HPLC pure product, N'-t-butoxycarbonyltrytophan-N-((methyl)aminoethyl)-amide as a white foam.
Workup
- customwas removed under high vacuum at 35° C
- dissolutionThe residue was dissolved in ethyl acetate (40 mL)
- extractionthe adduct was extracted into 1N HCl (3×25 mL)
- extractionThe combined aqueous extract
- extractionextracted with ethyl acetate (3×25 mL)
- extractionThe combined organic extract
- washwas washed with brine (30 mL)
- dry with materialdried (MgSO4)
- customEvaporation to dryness
Sources & evidence
- ORD record
- ord-933b68baf1c14fad8b38939bd157c7fe
- Source dataset
- uspto-grants-1998_06
- Patent number
- US05773428
Reaction notes
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