Tetrabutylammonium Fluoride → 2-(3-Tert-butoxycarbonyl-propoxy)-4-chloro-5-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-benzoic acid

HRID 448929Notes

Reaction equation

HRID 448929 reaction equation
C[Si](C)(C)CC[O:5][C:6](=[O:37])[C:7]1[CH:12]=[C:11]([C:13]2[CH:14]=[N:15][C:16]([C:21]([F:24])([F:23])[F:22])=[CH:17][C:18]=2[C:19]#[N:20])[C:10]([Cl:25])=[CH:9][C:8]=1[O:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:33]([O:32][C:30]([CH2:29][CH2:28][CH2:27][O:26][C:8]1[CH:9]=[C:10]([Cl:25])[C:11]([C:13]2[CH:14]=[N:15][C:16]([C:21]([F:23])([F:24])[F:22])=[CH:17][C:18]=2[C:19]#[N:20])=[CH:12][C:7]=1[C:6]([OH:37])=[O:5])=[O:31])([CH3:36])([CH3:34])[CH3:35]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 686032652-(3-Tert-butoxycarbonyl-propoxy)-4-chloro-5-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-benzoic acid 2-trimethylsilanyl-ethyl ester

Product 1

HCID 686028022-(3-Tert-butoxycarbonyl-propoxy)-4-chloro-5-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-benzoic acidYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(3-tert-butoxycarbonyl-propoxy)-4-chloro-5-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-benzoic acid 2-trimethylsilanyl-ethyl ester (1.3 g, 2.2 mmol) and tetrabutyl-ammonium fluoride (6.6 mL, 6.6 mmol, 1 M in THF) in THF (20 mL) was stirred at rt for 30 minutes. The mixture was then concentrated and diluted with ether. The ether layer was washed with water, dried and concentrated to yield 2-(3-tert-butoxycarbonyl-propoxy)-4-chloro-5-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-benzoic acid (0.8 g). MS [M+H]+: 485.1; tR=2.96 min (method 1)

Workup

  1. concentrationThe mixture was then concentrated
  2. additiondiluted with ether
  3. washThe ether layer was washed with water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4a28e25eb8384858aea73dc913570267
Source dataset
uspto-grants-2013_07
Patent number
US08481738B2

Reaction notes

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