Lithium hydroxide, monohydrate → 5'-(3-Furoylamino)-2'-methyl-1,1'-biphenyl-4-carboxylic acid

HRID 970226Notes

Reaction equation

HRID 970226 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([CH3:25])=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([O:23]C)=[O:22])=[CH:17][CH:16]=3)[CH:14]=2)=[O:7])=[CH:2]1.O.[OH-].[Li+]>C1COCC1.O>[O:1]1[CH:5]=[CH:4][C:3]([C:6]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([CH3:25])=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([OH:23])=[O:22])=[CH:17][CH:16]=3)[CH:14]=2)=[O:7])=[CH:2]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 69152621Methyl 5'-(3-furoylamino)-2'-methyl-1,1'-biphenyl-4-carboxylate

Product 1

HCID 691521465'-(3-Furoylamino)-2'-methyl-1,1'-biphenyl-4-carboxylic acidYield 77.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 5′-(3-furoylamino)-2′-methyl-1,1′-biphenyl-4-carboxylate (980 mg, 2.9 mmol) and lithium hydroxide monohydrate (256 mg, 6.1 mmol) in THF (12 ml) and water (6 ml) were heated at 75° C. for 18 h. The THF was evaporated under vacuum and the aqueous adjusted to pH3 with hydrochloric acid (1M). The precipitate which formed was filtered off, washed with ether and dried under vacuum to give 5′-(3-furoylamino)-2′-methyl-1,1′-biphenyl-4-carboxylic acid (720 mg, 77%). LCMS: retention time 3.33 min, MH+322.

Workup

  1. customThe THF was evaporated under vacuum
  2. customThe precipitate which formed
  3. filtrationwas filtered off
  4. washwashed with ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-282f1ffce03e4f39926b8ad5d3a7429e
Source dataset
uspto-grants-2007_12
Patent number
US07309800B2

Reaction notes

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