Sodium Hydroxide → 4-[4-(2-Adamantylcarbamoyl)-5-cyclopentylsulfanyl-pyrazol-1-yl]benzoic acid

HRID 1160511Notes

Reaction equation

[OH-].[Na+].[CH:3]12[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH:4]1[NH:13][C:14]([C:16]1[CH:17]=[N:18][N:19]([C:27]3[CH:36]=[CH:35][C:30]([C:31]([O:33]C)=[O:32])=[CH:29][CH:28]=3)[C:20]=1[S:21][CH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)=[O:15])[CH2:10]2>CO>[CH:3]12[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH:4]1[NH:13][C:14]([C:16]1[CH:17]=[N:18][N:19]([C:27]3[CH:36]=[CH:35][C:30]([C:31]([OH:33])=[O:32])=[CH:29][CH:28]=3)[C:20]=1[S:21][CH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)=[O:15])[CH2:10]2

Participants

Conditions

Temperature: 20 °C

Procedure

2M aqueous sodium hydroxide (1.694 mL, 3.39 mmol) was added in one portion to methyl 4-[4-(2-adamantylcarbamoyl)-5-cyclopentylsulfanyl-pyrazol-1-yl]benzoate (Intermediate #90) (325 mg, 0.68 mmol) in methanol (10 mL). The resulting mixture was stirred at 20° C. for 18 hours. The reaction mixture was concentrated and diluted with water (50 mL), and washed with ether (20 mL). The aqueous solution was adjusted to pH 3 with 2M HCl and extracted with EtOAc (2×25 mL), and the combined extracts washed sequentially with water (2×20 mL) and saturated brine (20 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford 4-[4-(2-adamantylcarbamoyl)-5-cyclopentylsulfanyl-pyrazol-1-yl]benzoic acid (307 mg, 97%).

Workup

concentrationThe reaction mixture was concentrated
additiondiluted with water (50 mL)
washwashed with ether (20 mL)
extractionextracted with EtOAc (2×25 mL)
washthe combined extracts washed sequentially with water (2×20 mL) and saturated brine (20 mL)
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-3d13231a129f4027830fb4bd23a7dbf0
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816391B2

Reaction notes

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