Tetrabutylammonium Fluoride → HCID 90370156, compound

HRID 2176022Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:33])[CH2:5][CH2:6][CH2:7][C:8]([N:10]([CH2:17][C:18]1[CH:19]=[C:20]([CH:30]=[CH:31][CH:32]=1)[C:21]([O:23]CC[Si](C)(C)C)=[O:22])[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)=[O:9])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>>[CH2:1]([O:3][C:4](=[O:33])[CH2:5][CH2:6][CH2:7][C:8]([N:10]([CH2:17][C:18]1[CH:19]=[C:20]([CH:30]=[CH:31][CH:32]=1)[C:21]([OH:23])=[O:22])[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)=[O:9])[CH3:2]

Participants

Reactant 2

HCID 2724141Tetrabutylammonium Fluoride

HCID 90370114HCID 90370114, compound

Product 1

HCID 90370156HCID 90370156, compoundYield 54.2%

Procedure

By using 375 mg of 2-(trimethylsilyl)ethyl 3-{[(5-ethoxy-5-oxopentanoyl)(pyridin-3-yl)amino]methyl}benzoate and 1.0 mL of 1.0 M TBAF (THF solution), 160 mg of 3-{[(5-ethoxy-5-oxopentanoyl)(pyridin-3-yl)amino]methyl}benzoic acid was obtained by the method similar to Preparation Example 22.

Sources & evidence

ORD record: ord-2311c4de007a4c61823f4d99fc1cb7d6
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09062032B2

Reaction notes

Loading…