Tetrahydrofuran → 6-(cis-2-(Tert-butoxycarbonylamino)cyclohexylamino)-2-chloro-5-fluoronicotinic acid

HRID 1620042Notes

Reaction equation

[OH-].[Na+].O1CCCC1.[C:8]([O:12][C:13]([NH:15][C@H:16]1[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]1[NH:22][C:23]1[C:32]([F:33])=[CH:31][C:26]([C:27]([O:29]C)=[O:28])=[C:25]([Cl:34])[N:24]=1)=[O:14])([CH3:11])([CH3:10])[CH3:9]>CO>[C:8]([O:12][C:13]([NH:15][C@H:16]1[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]1[NH:22][C:23]1[C:32]([F:33])=[CH:31][C:26]([C:27]([OH:29])=[O:28])=[C:25]([Cl:34])[N:24]=1)=[O:14])([CH3:11])([CH3:9])[CH3:10]

Participants

Conditions

Temperature: 65 °C

Procedure

A 1N sodium hydroxide aqueous solution (15 ml) was added to a solution of tetrahydrofuran (30 ml) and methanol (30 ml) containing methyl 6-(cis-2-(tert-butoxycarbonylamino)cyclohexylamino)-2-chloro-5-fluoronicotinate (3.00 g), followed by stirring at 65° C. for 2 hours. The reaction mixture was cooled to room temperature, the solvent was distilled away under reduced pressure, and a saturated aqueous ammonium chloride solution, tetrahydrofuran, and ethyl acetate were added. The organic layer was collected, washed with saturated saline, and dried over anhydrous magnesium sulfate, and the solvent was distilled away under reduced pressure. Colorless oily matter of 6-(cis-2-(tert-butoxycarbonylamino)cyclohexylamino)-2-chloro-5-fluoronicotinic acid (3.00 g) was thus obtained.

Workup

temperatureThe reaction mixture was cooled to room temperature
distillationthe solvent was distilled away under reduced pressure
additiona saturated aqueous ammonium chloride solution, tetrahydrofuran, and ethyl acetate were added
customThe organic layer was collected
washwashed with saturated saline
dry with materialdried over anhydrous magnesium sulfate
distillationthe solvent was distilled away under reduced pressure

Sources & evidence

ORD record: ord-df82b7ba1d544573b7354df30e5811c2
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772320B2

Reaction notes

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