Triethylamine → HCID 86676231, compound

HRID 1426486Notes

Reaction equation

[OH:1][CH2:2][CH:3]([N:7]([CH2:15][CH:16]=[CH2:17])[C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:4][CH:5]=[CH2:6].C(N(CC)CC)C.[N+:25]([C:28]1[CH:36]=[CH:35][C:31]([C:32](Cl)=[O:33])=[CH:30][CH:29]=1)([O-:27])=[O:26]>CN(C)C1C=CN=CC=1.ClCCl.C(=O)([O-])O.[Na+]>[N+:25]([C:28]1[CH:29]=[CH:30][C:31]([C:32]([O:1][CH2:2][CH:3]([N:7]([C:8]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:14])[CH2:15][CH:16]=[CH2:17])[CH2:4][CH:5]=[CH2:6])=[O:33])=[CH:35][CH:36]=1)([O-:27])=[O:26]

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of tert-butyl [1-(hydroxymethyl)but-3-en-1-yl]prop-2-en-1-ylcarbamate (15.0 g) produced above, triethylamine (19.0 g) and dichloromethane (150 mL) was added N,N-dimethylpyridin-4-amine (0.7 g). To the mixture was added dropwise a solution of 4-nitrobenzoyl chloride (14.2 g) in dichloromethane (30 mL), and the mixture was stirred at 0° C. for 30 min. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate, the mixture was extracted with dichloromethane, and the extract was dried over anhydrous sodium sulfate. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (14.1 g).

Workup

extractionthe mixture was extracted with dichloromethane
dry with materialthe extract was dried over anhydrous sodium sulfate
filtrationInsoluble material was filtered off
concentrationthe filtrate was concentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether)

Sources & evidence

ORD record: ord-8320f5734047438e83cc999a1eb6261f
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933069B2

Reaction notes

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