Lithium Hydroxide → HCID 50922914, compound

HRID 62724Notes

Reaction equation

HRID 62724 reaction equation
[OH-].[Li+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:21]=[C:22]([Cl:27])[C:23]=1[O:24][CH2:25][CH3:26])[C:7]([NH:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16]C)=[O:15])=[C:12]([CH3:20])[CH:11]=1)=[O:8]>O.C1COCC1>[Cl:3][C:4]1[CH:5]=[C:6]([CH:21]=[C:22]([Cl:27])[C:23]=1[O:24][CH2:25][CH3:26])[C:7]([NH:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([OH:16])=[O:15])=[C:12]([CH3:20])[CH:11]=1)=[O:8]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67041575Methyl 4-(3,5-dichloro-4-ethoxybenzamido)-2-methylbenzoate

Product 1

HCID 50922914HCID 50922914, compoundYield 22.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (60 mg, 2.51 mmol) in water (1 mL) was added dropwise to a stirring solution of methyl 4-(3,5-dichloro-4-ethoxybenzamido)-2-methylbenzoate (3) (267 mg, 56%) (240 mg, 0.628 mmol) in THF (5 mL) and the resulting yellow solution was stirred for 5 days at RT. The solvent was evaporated in vacuo and dissolved in water (5 mL), then acidified with 2 M HCl. The resultant mixture was extracted with EtOAc. The organic layer was washed with water, dried over MgSO4 and filtered and pre-adsorbed on silica. Silica gel chromatography (40 g, 0-10% IPA in DCM) provided 4-(3,5-dichloro-4-ethoxybenzamido)-2-methylbenzoic acid (AAA-019) (52 mg, 22%): m/z 366 (M−H)− (ES−). 1H NMR (400 MHz, DMSO-d6) δ: 12.66 (1H, s), 10.49 (1H, s), 8.08 (2H, s), 7.87 (1H, d), 7.71 (1H, dd), 7.68 (1H, d), 4.14 (2H, q), 2.54 (3H, s), 1.40 (2H, t).

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutiondissolved in water (5 mL)
  3. extractionThe resultant mixture was extracted with EtOAc
  4. washThe organic layer was washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered and pre-adsorbed on silica

Sources & evidence

ORD record
ord-f59218c508c84a338464ba15c433a48b
Source dataset
uspto-grants-2016_09
Patent number
US09447028B2

Reaction notes

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