Hydrochloric Acid → HCID 69216116, compound

HRID 2221980Notes

Reaction equation

HRID 2221980 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:40])=[C:9]([CH2:11][O:12][C:13]2[CH:37]=[CH:36][C:16]([CH2:17][O:18][C:19]3[C:24]([C:25]([O:27]CC)=[O:26])=[CH:23][N:22]=[C:21]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[N:20]=3)=[CH:15][C:14]=2[O:38][CH3:39])[N:10]=1.O1CCCC1.[OH-].[Na+].Cl>O.C(O)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:40])=[C:9]([CH2:11][O:12][C:13]2[CH:37]=[CH:36][C:16]([CH2:17][O:18][C:19]3[C:24]([C:25]([OH:27])=[O:26])=[CH:23][N:22]=[C:21]([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:20]=3)=[CH:15][C:14]=2[O:38][CH3:39])[N:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 69217713HCID 69217713, compound

Product 1

HCID 69216116HCID 69216116, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of ethyl 4-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-2-phenylpyrimidine-5-carboxylate (0.47 g), tetrahydrofuran (10 mL) and ethanol (10 mL) was added 1N aqueous sodium hydroxide solution (3 mL), and the mixture was stirred at 60° C. for 1 hr. The reaction mixture was poured into water, 2N hydrochloric acid was added to acidify the solution, and the precipitated crystals were collected by filtration. Recrystallized from methanol-ethyl acetate gave 4-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-2-phenylpyrimidine-5-carboxylic acid as pale-yellow needle crystals (0.18 g, yield 40%). melting point: 163-164° C.

Workup

  1. additionwas added
  2. filtrationthe precipitated crystals were collected by filtration
  3. customRecrystallized from methanol-ethyl acetate

Sources & evidence

ORD record
ord-5383609f2f7b4de79990fb2eef7e1c23
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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