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

HRID 1848641Notes

Reaction equation

HRID 1848641 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-1860eef0b0d8481287e788369c9d26e5
Source dataset
uspto-grants-2015_02
Patent number
US08952161B2

Reaction notes

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