Dicyclohexylcarbodiimide → HCID 67616063, compound

HRID 965164Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@H:9]([C:20]([OH:22])=O)[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].[NH2:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][OH:29].ON1C2C=CC=CC=2N=N1.C1CCC(N=C=NC2CCCCC2)CC1>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)[NH:13][CH:12]=1)[C:20]([NH:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][OH:29])=[O:22])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of N-t-butoxycarbonyl-L-tryptophan, (128 g, 0.42 mol), 2-(2-aminoethoxy)ethanol (46.42 g, 0.44 mol), 1-hydroxybenzotriazole (60.0 g, 0.44 mol) in 700 mL of DMF at 0° C. was added DCC (100 g, 0.48 mol). After stirring at 0° C. for 15 minutes, the mixture was stirred at room temperature overnight. The white solids were filtered and washed with EtOAc. The filtrate was concentrated under reduced pressure. The residue was taken up in ether and a small amount of EtOAc, washed with it HCl (3×500 mL), saturated NaHCO3 (3×500 mL), and brine (3×500 mL). The organic layer was dried (MgSO4), filtered and concentrated to give 2-(S)-t-butoxycarbonylamino-N-[2-(2-hydroxy-ethoxy)ethyl]-3-(1H-indol-3-yl)-propionamide, 150 g (yield 91%), MS: 392.2 (M+H)+.

Workup

stirringthe mixture was stirred at room temperature overnight
filtrationThe white solids were filtered
washwashed with EtOAc
concentrationThe filtrate was concentrated under reduced pressure
washa small amount of EtOAc, washed with it HCl (3×500 mL), saturated NaHCO3 (3×500 mL), and brine (3×500 mL)
dry with materialThe organic layer was dried (MgSO4)
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-1a8540d510154d078ed11e012c3eb831
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05773428

Reaction notes

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