Hydrochloric Acid → 8-[(2R)-(1-(3-fluorophenyl)pyrrolidin-2-yl)]-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid

HRID 41193Notes

Reaction equation

[OH-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([N:10]2[CH2:14][CH2:13][CH2:12][C@@H:11]2[C:15]2[CH:16]=[C:17]([C:32]([O:34]C)=[O:33])[CH:18]=[C:19]3[C:24]=2[O:23][C:22]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[CH:21][C:20]3=[O:31])[CH:7]=[CH:8][CH:9]=1.Cl>C1COCC1.CO>[F:3][C:4]1[CH:5]=[C:6]([N:10]2[CH2:14][CH2:13][CH2:12][C@@H:11]2[C:15]2[CH:16]=[C:17]([C:32]([OH:34])=[O:33])[CH:18]=[C:19]3[C:24]=2[O:23][C:22]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[CH:21][C:20]3=[O:31])[CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 25 °C

Procedure

NaOH 2N (0.398 mL, 0.80 mmol) was added to methyl 8-[(2R)-(1-(3-fluorophenyl)pyrrolidin-2-yl)]-2-morpholino-4-oxo-4H-chromene-6-carboxylate (120 mg, 0.27 mmol) in a mixture of THF (2.4 mL) and MeOH (2.4 mL). The resulting solution was stirred at 25° C. over the weekend. HCl aq was added until pH ˜2. The solvents were removed under vacuum and the yellow solid was collected by filtration, washed with Diethyl ether to give 8-[(2R)-(1-(3-fluorophenyl)pyrrolidin-2-yl)]-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid (100 mg, 86%). Mass Spectrum: m/z [M+H]+=439.

Workup

customThe solvents were removed under vacuum
filtrationthe yellow solid was collected by filtration
washwashed with Diethyl ether

Sources & evidence

ORD record: ord-8640e8e997894af0af29e347633db6ad
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530470B2

Reaction notes

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