Hydrochloric Acid → HCID 178489257, compound

HRID 423199Notes

Reaction equation

[C:1]([C:5]1[C:6]2[CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][CH3:20])[N:11]([C:21]3[CH:26]=[CH:25][C:24]([C:27]4[O:31][N:30]=[C:29]([C:32]([O:34]CC)=[O:33])[CH:28]=4)=[CH:23][CH:22]=3)[C:10](=[O:37])[C:7]=2[NH:8][N:9]=1)([CH3:4])([CH3:3])[CH3:2].CO.[OH-].[Na+].Cl>O.C1COCC1>[C:1]([C:5]1[C:6]2[CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][CH3:20])[N:11]([C:21]3[CH:26]=[CH:25][C:24]([C:27]4[O:31][N:30]=[C:29]([C:32]([OH:34])=[O:33])[CH:28]=4)=[CH:23][CH:22]=3)[C:10](=[O:37])[C:7]=2[NH:8][N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of 3-t-butyl-5-[4-(3-ethoxycarbonyl-5-isoxazolyl)phenyl]-4-(2-methoxyphenyl)-4,5-dihydro-1H-pyrrolo[3,4-c]pyrazol-6-one (1.26 g, 2.5 mmol), methanol (4 mL), THF (4 mL) and water (3 mL), 2N aqueous sodium hydroxide (1.5 mL, 3 mmol) was added and the mixture was stirred at 50° C. for 1 hr. Water (40 mL) and 1N hydrochloric acid (2 mL) were added to the mixture, which was then extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product was suspended in ether, and the precipitate was collected to give 3-t-butyl-5-[4-(3-carboxy-5-isoxazolyl)phenyl]-4-(2-methoxyphenyl)-4,5-dihydro-1H-pyrrolo[3,4-c]pyrazol-6-one (0.84 g, 71%) as pale yellow crystals.

Workup

additionwas added
extractionwas then extracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customthe precipitate was collected

Sources & evidence

ORD record: ord-0e0c29df37714b2ebe85a6252eeaae8e
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101644B2

Reaction notes

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