Tetrabutylammonium Fluoride → 2-(2-tert-Butoxycarbonyl-ethyl)-5-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzoic acid

HRID 1181107Notes

Reaction equation

HRID 1181107 reaction equation
C[Si](C)(C)CC[O:5][C:6](=[O:37])[C:7]1[CH:12]=[C:11]([O:13][CH2:14][CH2:15][C:16]2[N:17]=[C:18]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[O:19][C:20]=2[CH3:21])[CH:10]=[CH:9][C:8]=1[CH2:28][CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:33]([O:32][C:30]([CH2:29][CH2:28][C:8]1[CH:9]=[CH:10][C:11]([O:13][CH2:14][CH2:15][C:16]2[N:17]=[C:18]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[O:19][C:20]=2[CH3:21])=[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 589792942-(2-Tert-butoxycarbonyl-ethyl)-5-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzoic acid 2-trimethylsilanylethyl ester

Product 1

HCID 179843812-(2-tert-Butoxycarbonyl-ethyl)-5-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzoic acidYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(2-tert-butoxycarbonyl-ethyl)-5-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzoic acid 2-trimethylsilanylethyl ester (5.04 g, 9.13 mmol) in THF (100 mL) was treated with TBAF (20 mL, 1.0 M) at room temperature for 1 h. The reaction mixture was concentrated and purified using silica gel chromatography (hexanes/EtOAc 1/1) to afford the title compound as a colorless oil (4.04 g, 98%). 1H NMR (400 MHz, CDCl3): δ 1.38 (s, 9H), 2.37 (s, 3H), 2.55 (t, 2H, J=7.3 Hz), 2.98 (t, 2H, J=6.5 Hz), 3.15 (t, 2H, J=7.3 Hz), 4.26 (t, 2H, J=6.5 Hz), 4.35 (t, 2H, J=8.8 Hz), 6.99 (dd, 1H, J=2.9, 8.8 Hz), 7.18 (d, 1H, J=8.3 Hz), 7.38-7.43 (m, 3H), 7.49 (d, 1H, J=2.9 Hz), 7.97 (d, 2H, J=7.8 Hz). MS (ES) m/z 522.3 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified

Sources & evidence

ORD record
ord-418bc38b7f154379b95bc73d3cb797cb
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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