Lithium Hydroxide → 5-(Hydroxy(thiazol-2-yl)methyl)-4'-methylbiphenyl-3-carboxylic acid

HRID 1845299Notes

Reaction equation

HRID 1845299 reaction equation
[OH:1][CH:2]([C:20]1[S:21][CH:22]=[CH:23][N:24]=1)[C:3]1[CH:4]=[C:5]([C:16]([O:18]C)=[O:17])[CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH:8]=1.[OH-].[Li+].[NH4+].[Cl-]>O1CCOCC1.O>[OH:1][CH:2]([C:20]1[S:21][CH:22]=[CH:23][N:24]=1)[C:3]1[CH:4]=[C:5]([C:16]([OH:18])=[O:17])[CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH:8]=1

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 25517Ammonium ChlorideHCID 58188318Methyl 5-(hydroxy(thiazol-2-yl)methyl)-4'-methylbiphenyl-3-carboxylate

Product 1

HCID 581881135-(Hydroxy(thiazol-2-yl)methyl)-4'-methylbiphenyl-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of methyl 5-(hydroxy(thiazol-2-yl)methyl)-4′-methylbiphenyl-3-carboxylate (170 mg, 0.50 mmol) in 1,4-dioxane (1.5 mL) and water (1.5 mL) was added lithium hydroxide (42 mg, 1.8 mmol). After being stirred at rt for 4 h, the reaction mixture was treated with aq. NH4Cl and extracted with EtOAc (15 mL×3). The combined organic layers were dried over anhydrous MgSO4 and purified by silica gel column to afford the title compound. 1H NMR (CDCl3, 400 MHz): 8.19 (s, 1H), 8.16 (s, 1H), 7.86 (s, 1H), 7.72 (d, J=2.4 Hz, 1H), 7.41 (d, J=7.6 Hz, 2H), 7.24 (m, 1H), 7.14 (d, J=7.6 Hz, 2H), 6.21 (s, 1H), 5.28 (s, 1H), 2.32 (s, 3H).

Workup

  1. extractionextracted with EtOAc (15 mL×3)
  2. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  3. custompurified by silica gel column

Sources & evidence

ORD record
ord-ed64fb6338584647959bd7faef7d38eb
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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