Hydrochloric Acid → HCID 86672443, compound

HRID 41226Notes

Reaction equation

[OH-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([N:10]2[CH2:14][CH2:13][CH2:12][CH:11]2[C:15]2[CH:16]=[C:17]([C:33]([O:35]C)=[O:34])[CH:18]=[C:19]3[C:24]=2[O:23][C:22]([N:25]2[CH2:30][CH2:29][O:28][C@H:27]([CH3:31])[CH2:26]2)=[CH:21][C:20]3=[O:32])[CH:7]=[CH:8][CH:9]=1.Cl>CO>[F:3][C:4]1[CH:5]=[C:6]([N:10]2[CH2:14][CH2:13][CH2:12][CH:11]2[C:15]2[CH:16]=[C:17]([C:33]([OH:35])=[O:34])[CH:18]=[C:19]3[C:24]=2[O:23][C:22]([N:25]2[CH2:30][CH2:29][O:28][C@H:27]([CH3:31])[CH2:26]2)=[CH:21][C:20]3=[O:32])[CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 40 °C

Procedure

An aqueous NaOH 2N (0.804 ml, 1.61 mmol) solution was added to methyl 8-(1-(3-fluorophenyl)pyrrolidin-2-yl)-2-((R)-2-methylmorpholino)-4-oxo-4H-chromene-6-carboxylate (0.25 g, 0.54 mmol) suspended in MeOH (4 mL). The solution was stirred at 40° C. overnight then cooled to 0° C. and an aqueous HCl 2N (0.670 ml, 1.34 mmol) solution was added dropwise to the reaction mixture until pH ˜3. The resulting precipitate was collected by filtration, washed with water and dried under vacuum at 50° C. in presence of P2O5 to a constant weight to afford 8-(1-(3-fluorophenyl)pyrrolidin-2-yl)-2-((R)-2-methylmorpholino)-4-oxo-4H-chromene-6-carboxylic acid (201 mg, 83%) as a beige solid. Mass Spectrum: m/z [M+H]+=453.

Workup

temperaturethen cooled to 0° C.
filtrationThe resulting precipitate was collected by filtration
washwashed with water
dry with materialdried under vacuum at 50° C. in presence of P2O5 to a constant weight

Sources & evidence

ORD record: ord-f6ae09abdbd74830853f865981d94c9e
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530470B2

Reaction notes

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