Lithium Hydroxide → HCID 51034187, compound

HRID 62743Notes

Reaction equation

HRID 62743 reaction equation
[OH-].[Li+].[CH:3]([O:6][C:7]1[CH:8]=[C:9]([CH:23]=[C:24]([O:29][CH:30]([CH3:32])[CH3:31])[C:25]=1[O:26][CH2:27][CH3:28])[C:10]([NH:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([O-:19])=[O:18])=[C:15]([F:22])[CH:14]=1)=[O:11])([CH3:5])[CH3:4]>C1COCC1>[CH:3]([O:6][C:7]1[CH:8]=[C:9]([CH:23]=[C:24]([O:29][CH:30]([CH3:31])[CH3:32])[C:25]=1[O:26][CH2:27][CH3:28])[C:10]([NH:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[C:15]([F:22])[CH:14]=1)=[O:11])([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86666598HCID 86666598, compound

Product 1

HCID 51034187HCID 51034187, compoundYield 56.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2 M Lithium hydroxide (554 μL, 1.11 mmol) was added to a solution of 4-(3,5-diisopropoxy-4-ethoxybenzamido)-2-fluorobenzoate (3) (320 mg, 0.740 mmol) in THF (5 mL) and the mixture was stirred at RT for 20 h. The mixture was partitioned between 1M HCl (5 mL) and DCM (10 mL) and the phases were separated. The organic solvent was removed in vacuo and the residue was purified by silica gel chromatography (40 g, 0-20% IPA in isohexane) to afford 4-(3,5-diisopropoxy-4-ethoxybenzamido)-2-fluorobenzoic acid (AAA-064) as a white solid (176 mg, 56%): m/z 420 [M+H]+ (ES+), 418 [M−H]− (ES−). 1H-NMR (400 MHz, DMSO-d6) δ: 13.03 (1H, br s), 10.45 (1H, s), 7.88 (1H, t), 7.81 (1H, dd), 7.61 (1H, dd), 7.22 (2H, s), 4.65 (2H, sep), 4.00 (2H, q), 1.29 (12H, d), 1.26 (3H, t).

Workup

  1. customThe mixture was partitioned between 1M HCl (5 mL) and DCM (10 mL)
  2. customthe phases were separated
  3. customThe organic solvent was removed in vacuo
  4. customthe residue was purified by silica gel chromatography (40 g, 0-20% IPA in isohexane)

Sources & evidence

ORD record
ord-72d1cb29de514e8b92eda89af5958294
Source dataset
uspto-grants-2016_09
Patent number
US09447028B2

Reaction notes

Loading…