Tetrabutylammonium Fluoride → 4-[((4-Carboxybutyl)[2-[2-([4-[2-(4-hydroxyphenyl)ethyl]benzyl]oxy)phenyl]-ethyl]amino)methyl]benzoic acid

HRID 8139Notes

Reaction equation

HRID 8139 reaction equation
C([Si](C)(C)[O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]2[CH:51]=[CH:50][C:18]([CH2:19][O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH2:27][CH2:28][N:29]([CH2:39][C:40]3[CH:49]=[CH:48][C:43]([C:44]([O:46]C)=[O:45])=[CH:42][CH:41]=3)[CH2:30][CH2:31][CH2:32][CH2:33][C:34]([O:36]CC)=[O:35])=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:34]([CH2:33][CH2:32][CH2:31][CH2:30][N:29]([CH2:39][C:40]1[CH:49]=[CH:48][C:43]([C:44]([OH:46])=[O:45])=[CH:42][CH:41]=1)[CH2:28][CH2:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[O:20][CH2:19][C:18]1[CH:50]=[CH:51][C:15]([CH2:14][CH2:13][C:10]2[CH:9]=[CH:8][C:7]([OH:6])=[CH:12][CH:11]=2)=[CH:16][CH:17]=1)([OH:36])=[O:35]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 23546389Methyl 4-{[{2-[2-({4-[2-(4-{[tert-butyl(dimethyl)-silyl]oxy}phenyl)ethyl]benzyl}oxy)phenyl]ethyl}(5-ethoxy-5-oxopentyl)amino]-methyl}benzoate

Product 1

HCID 235462664-[((4-Carboxybutyl)[2-[2-([4-[2-(4-hydroxyphenyl)ethyl]benzyl]oxy)phenyl]-ethyl]amino)methyl]benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

27 mg (0.037 mmol) of methyl 4-{[{2-[2-({4-[2-(4-{[tert-butyl(dimethyl)-silyl]oxy}phenyl)ethyl]benzyl}oxy)phenyl]ethyl}(5-ethoxy-5-oxopentyl)amino]-methyl}benzoate from XXI are dissolved in 10 ml of THF. 0.03 ml of tetrabutylammonium fluoride (IM solution in THF) are added, and the solution is stirred at RT for 1 hour. The solvents are evaporated under reduced pressure. The residue is dissolved in 2 ml of methanol. 0.05 ml of aqueous sodium hydroxide solution, 45%, and 0.2 ml of dichloromethane are added, and the solution is stirred at RT for 8 hours. The mixture is concentrated, water is added and the solution is acidified using sulphuric acid. The solid is filtered off and dried.

Workup

  1. customThe solvents are evaporated under reduced pressure
  2. dissolutionThe residue is dissolved in 2 ml of methanol
  3. addition0.05 ml of aqueous sodium hydroxide solution, 45%, and 0.2 ml of dichloromethane are added
  4. stirringthe solution is stirred at RT for 8 hours
  5. concentrationThe mixture is concentrated
  6. additionwater is added
  7. filtrationThe solid is filtered off
  8. customdried

Sources & evidence

ORD record
ord-3350d545ae14418b8df6f55ce8d0020d
Source dataset
uspto-grants-2006_08
Patent number
US07087644B1

Reaction notes

Loading…