Hydrochloric Acid → 5-({(2S)-2-[(tert-butoxycarbonyl)amino]propyl}oxy)-3-fluoropyridine-2-carboxylic acid

HRID 1026220Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH3:24])[CH2:10][O:11][C:12]1[CH:13]=[C:14]([F:23])[C:15]([C:18]([O:20]CC)=[O:19])=[N:16][CH:17]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1COCC1.[OH-].[Li+].Cl>C(O)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH3:24])[CH2:10][O:11][C:12]1[CH:13]=[C:14]([F:23])[C:15]([C:18]([OH:20])=[O:19])=[N:16][CH:17]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of ethyl 5-({(2S)-2-[(tert-butoxycarbonyl)amino]propyl}oxy)-3-fluoropyridine-2-carboxylate (402 mg), THF (4 mL), ethanol (4 mL) and 1M aqueous lithium hydroxide solution (4 mL) was stirred at 0° C. for 3 hr. The reaction mixture was neutralized with 1M hydrochloric acid at 0° C., and extracted with ethyl acetate. The combined organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (357 mg).

Workup

extractionextracted with ethyl acetate
washThe combined organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-fbf70f2a11c84b3daf13db9e5358e92e
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729102B2

Reaction notes

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