Toluene → HCID 178469807, compound

HRID 1967451Notes

Reaction equation

[Br:1][C:2]1[C:3]([O:33][CH3:34])=[CH:4][C:5](OC)=[C:6]([CH:30]=1)[C:7]([C:9](=[CH:15][NH:16][C@H:17]([C:21]([CH3:29])([CH3:28])[O:22][SiH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH:18]([CH3:20])[CH3:19])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:8].C1(C)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].O1CCCC1>[Br-].C([P+](CCCC)(CCCC)CCCC)CCC.[Cl-].[Na+].O>[Br:1][C:2]1[CH:30]=[C:6]2[C:5](=[CH:4][C:3]=1[O:33][CH3:34])[N:16]([C@H:17]([C:21]([CH3:28])([CH3:29])[O:22][SiH2:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH:18]([CH3:19])[CH3:20])[CH:15]=[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:7]2=[O:8]

Participants

Conditions

Temperature: 110 °C

Procedure

Under a nitrogen atmosphere, ethyl 2-(5-bromo-2,4-dimethoxybenzoyl)-3-((S)-1-(tert-butyldimethyl-silanyloxymethyl)-2-methylpropylamino)acrylate (5.0 g) was added to toluene (30 mL), and potassium carbonate (1.24 g) and tetra-n-butylphosphoniumbromide (1.52 g) were added. After stirring at 110° C. for 11 hr, the completion of the reaction was confirmed by HPLC. After cooling the reaction mixture, tetrahydrofuran (40 mL) and 10% brine (40 mL) were added, and the toluene layer was separated. The toluene layer was washed twice with 10% brine (40 mL). After washing, toluene was evaporated under reduced pressure to give crude ethyl 6-bromo-1-((S)-1-(tert-butyldimethyl-silanyloxymethyl)-2-methylpropyl)-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate.

Workup

additionwere added
additionwere added
customthe toluene layer was separated
washThe toluene layer was washed twice with 10% brine (40 mL)
washAfter washing
customtoluene was evaporated under reduced pressure

Sources & evidence

ORD record: ord-5fa83583a9474d0e817500cad88a642d
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420821B2

Reaction notes

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