1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 123772393, compound

HRID 514307Notes

Reaction equation

[Br:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[NH:5][C:4](=[O:10])[C:3]=1[CH3:11].[CH3:12][Si:13]([CH3:20])([CH3:19])[CH2:14][CH2:15][O:16][CH2:17]Cl.N12CCCN=C1CCCCC2>C(#N)C>[Br:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[N:5]([CH2:17][O:16][CH2:15][CH2:14][Si:13]([CH3:20])([CH3:19])[CH3:12])[C:4](=[O:10])[C:3]=1[CH3:11]

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of C2 (21.9 g, 99.8 mmol) and 2-(trimethylsilyl)ethoxymethyl chloride (20 g, 120 mmol) in acetonitrile (400 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 18.3 g, 120 mmol), and the reaction mixture was stirred at 60° C. for 18 hours. Additional 2-(trimethylsilyl)ethoxymethyl chloride (5 g, 30 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (4.6 g, 30 mmol) were added, and stirring was continued at 60° C. for 18 hours. After the mixture had been concentrated in vacuo, the residue was diluted with water (500 mL) and extracted with ethyl acetate (3×300 mL). The combined organic layers were concentrated; purification using chromatography on silica gel (Gradient: 20% to 50% ethyl acetate in petroleum ether) afforded the product as a colorless oil. Yield: 22.5 g, 64.4 mmol, 64%. 1H NMR (400 MHz, CDCl3) δ 5.41 (s, 2H), 3.61-3.72 (m, 5H), 2.13 (s, 3H), 0.93-1.02 (m, 2H), 0.00 (s, 9H).

Workup

stirringstirring
waitwas continued at 60° C. for 18 hours
concentrationAfter the mixture had been concentrated in vacuo
additionthe residue was diluted with water (500 mL)
extractionextracted with ethyl acetate (3×300 mL)
concentrationThe combined organic layers were concentrated
custompurification

Sources & evidence

ORD record: ord-9f9eb7fd35614d57a5bcebdd5c93706b
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09107923B2

Reaction notes

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