Hydrochloric Acid → [[2-[(4-Acetyl-3-hydroxy-2-propylbenzyl)thio]-pyrimidin-4-yl]oxy]acetic acid

HRID 2107102Notes

Reaction equation

[C:1]([C:4]1[CH:24]=[CH:23][C:7]([CH2:8][S:9][C:10]2[N:15]=[C:14]([O:16][CH2:17][C:18]([O:20]CC)=[O:19])[CH:13]=[CH:12][N:11]=2)=[C:6]([CH2:25][CH2:26][CH3:27])[C:5]=1[OH:28])(=[O:3])[CH3:2].[OH-].[Na+].C(OCC)(=O)C.Cl>CO>[C:1]([C:4]1[CH:24]=[CH:23][C:7]([CH2:8][S:9][C:10]2[N:15]=[C:14]([O:16][CH2:17][C:18]([OH:20])=[O:19])[CH:13]=[CH:12][N:11]=2)=[C:6]([CH2:25][CH2:26][CH3:27])[C:5]=1[OH:28])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

In 2 ml of 90% methanol was dissolved 0.06 g of ethyl [[2-[(4-acetyl-3-hydroxy-2-propylbenzyl)thio]-pyrimidin-4-yl]oxy]acetate obtained in Example 15 with heating at 60° C. Further 1 ml of a 1N aqueous sodium hydroxide solution was added to the solution followed by stirring at 60° C. for 15 minutes. An aqueous sodium hydroxide solution and ethyl acetate were added to the reaction mixture to fractionate. The aqueous phase was made acidic with 2N hydrochloric acid and extracted with ethyl acetate. The extract was washed with water and then dried over anhydrous magnesium sulfate. The solvent was then distilled off. The thus obtained solid was recrystallized from isopropyl alcohol to give 0.02 g of [[2-[(4-acetyl-3-hydroxy-2-propylbenzyl)thio]-pyrimidin-4-yl]oxy]acetic acid.

Workup

extractionextracted with ethyl acetate
washThe extract was washed with water
dry with materialdried over anhydrous magnesium sulfate
distillationThe solvent was then distilled off
customThe thus obtained solid was recrystallized from isopropyl alcohol

Sources & evidence

ORD record: ord-ff3cf864f4d34372809738c74375b8f9
Source dataset: uspto-grants-1990_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04933348

Reaction notes

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