Sodium Hydroxide → 4-(5-{3-[5-(4-Methoxy-phenyl)-oxazol-2-yl]-phenyl}-[1,3,4]oxadiazol-2-ylmethyl)-benzoic Acid

HRID 349451Notes

Reaction equation

HRID 349451 reaction equation
C[O:2][C:3](=[O:35])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[O:12][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]4[O:23][C:24]([C:27]5[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=5)=[CH:25][N:26]=4)[CH:17]=3)=[N:14][N:15]=2)=[CH:6][CH:5]=1.[OH-].[Na+]>C1COCC1.CO.O>[CH3:34][O:33][C:30]1[CH:29]=[CH:28][C:27]([C:24]2[O:23][C:22]([C:18]3[CH:17]=[C:16]([C:13]4[O:12][C:11]([CH2:10][C:7]5[CH:6]=[CH:5][C:4]([C:3]([OH:35])=[O:2])=[CH:9][CH:8]=5)=[N:15][N:14]=4)[CH:21]=[CH:20][CH:19]=3)=[N:26][CH:25]=2)=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 588048584-(5-{3-[5-(4-Methoxy-phenyl)-oxazol-2-yl]-phenyl}-[1,3,4]oxadiazol-2-ylmethyl)-benzoic Acid Methyl Ester

Product 1

HCID 588048474-(5-{3-[5-(4-Methoxy-phenyl)-oxazol-2-yl]-phenyl}-[1,3,4]oxadiazol-2-ylmethyl)-benzoic AcidYield 28.3%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A solution of 0.25 g (0.53 mmol) 4-(5-{3-[5-(4-Methoxy-phenyl)-oxazol-2-yl]-phenyl}-[1,3,4]oxadiazol-2-ylmethyl)-benzoic acid methyl ester from Example B2a in a 5:2:1 mixture of THF/methanol/water was added 1.0 mL (1.0 mmol) 1N NaOH. The mixture was stirred 14 hours at room temperature before concentrating on a rotary evaporator. Partitioned between ether and water. Separated layers and acidified aqueous layer with 6M HCl. Extracted aqueous layer with 1:1 Et2O/EtOAc (2×), combined organic layers and wash with saturated aqueous NaCl solution and dried (MgSO4). Obtained a solid from MeOH. Filter and dry in a vacuum oven overnight at room temperature to provide 0.068 g (28%) desired product.

Workup

  1. concentrationbefore concentrating on a rotary evaporator
  2. customPartitioned between ether and water
  3. washwash with saturated aqueous NaCl solution
  4. dry with materialdried (MgSO4)
  5. customObtained a solid from MeOH
  6. filtrationFilter
  7. customdry in a vacuum oven overnight at room temperature

Sources & evidence

ORD record
ord-690557ad2dd74aae95dca0f73c27bbb8
Source dataset
uspto-grants-2007_02
Patent number
US07179822B2

Reaction notes

Loading…