Sodium Hydroxide → 4-{[3-(4-Chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]methyl}-3-methoxybenzenecarboxylic acid

HRID 536541Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]3[CH2:15][CH2:14]3)[C:11](=[O:16])[N:10]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([O:26]C)=[O:25])=[CH:20][C:19]=3[O:28][CH3:29])[N:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCCC1.CO.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]3[CH2:14][CH2:15]3)[C:11](=[O:16])[N:10]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([OH:26])=[O:25])=[CH:20][C:19]=3[O:28][CH3:29])[N:9]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

An amount of 830 mg (2.01 mmol) of the compound from Example 20A was dissolved in 10 ml of tetrahydrofuran/methanol (1:1) and admixed with 2 ml of a 2 N sodium hydroxide solution (4.01 mmol). The mixture was stirred at 80° C. for an hour. The reaction solution was diluted with 10 ml of water and extracted with twice 15 ml of ethyl acetate. The combined organic phases did not contain a product and were discarded. The aqueous product phase was acidified with 1 N hydrochloric acid and the resulting precipitate was isolated by filtration. The solid was dried in a high vacuum. Since the mother liquor still contained a large amount of product, it was concentrated completely on a rotary evaporator. This gave, all in all, 747 mg (93% of theory) of the target compound.

Workup

extractionextracted with twice 15 ml of ethyl acetate
customthe resulting precipitate was isolated by filtration
customThe solid was dried in a high vacuum
concentrationwas concentrated completely on a rotary evaporator

Sources & evidence

ORD record: ord-b232e55aa8db43608d3db7467e86cfcf
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859601B2

Reaction notes

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