Diisopropylethylamine → HCID 86714704, compound

HRID 529220Notes

Reaction equation

[C:1]([O:5][C:6]([C:8]1[S:9][C:10]([CH2:13][NH:14][CH2:15][CH:16]([CH3:18])[CH3:17])=[CH:11][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:19][O:20][C:21](=[O:38])[C@H:22]([CH2:33][C:34]([O:36][CH3:37])=[O:35])[NH:23][C:24](OC1C=CC=CC=1)=[O:25].C(N(CC)C(C)C)(C)C>C(#N)C>[CH3:19][O:20][C:21](=[O:38])[C@H:22]([CH2:33][C:34]([O:36][CH3:37])=[O:35])[NH:23][C:24]([N:14]([CH2:13][C:10]1[S:9][C:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:12][CH:11]=1)[CH2:15][CH:16]([CH3:18])[CH3:17])=[O:25]

Participants

Conditions

Temperature: 60 °C

Procedure

The compound (1.1 g, 4.1 mmol) obtained in step 1 and the compound (1.2 g, 4.1 mmol) obtained in step 2 were dissolved in acetonitrile (40 ml), N,N-diisopropylethylamine (0.71 mL, 4.1 mmol) was added, and the mixture was stirred at 60° C. for 2 hours. The solvent was evaporated under reduced pressure, ethyl acetate was added, and the mixture was washed with water and saturated brine. After drying over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound.

Workup

customThe solvent was evaporated under reduced pressure, ethyl acetate
additionwas added
washthe mixture was washed with water and saturated brine
dry with materialAfter drying over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customthe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-0aa283c3a8834d2e95d5aac534e703f5
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346821B2

Reaction notes

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