Methanol → (5-{2-[(N-Cyclopropanecarbonyl-N-ethyl-amino)-methyl]-4-fluoro-phenyl}-pyridin-3-yl)-acetic acid

HRID 554640Notes

Reaction equation

C([O:3][C:4](=[O:28])[CH2:5][C:6]1[CH:7]=[N:8][CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[CH2:19][N:20]([C:23]([CH:25]2[CH2:27][CH2:26]2)=[O:24])[CH2:21][CH3:22])[CH:11]=1)C.[Li+].[OH-].CO>C1COCC1>[CH:25]1([C:23]([N:20]([CH2:19][C:13]2[CH:14]=[C:15]([F:18])[CH:16]=[CH:17][C:12]=2[C:10]2[CH:11]=[C:6]([CH2:5][C:4]([OH:28])=[O:3])[CH:7]=[N:8][CH:9]=2)[CH2:21][CH3:22])=[O:24])[CH2:27][CH2:26]1

Participants

Conditions

Temperature: 35 °C

Procedure

(5-{2-[(N-Cyclopropanecarbonyl-N-ethyl-amino)-methyl]-4-fluoro-phenyl}-pyridin-3-yl)-acetic acid ethyl ester (0.202 g, 0.53 mmol) was dissolved in THF (5.25 mL) and treated with 1N aqueous LiOH (2.63 mL, 2.63 mmol) and a small amount of MeOH. The reaction was stirred at 35° C. for 30 minutes. The mixture was concentrated, and the residue was diluted with H2O and washed with EtOAc. The aqueous layer was acidified with 1N aqueous HCl to pH 6 and extracted with EtOAc, and the combined organic layers were washed with H2O and brine, and then dried over Na2SO4, filtered, and concentrated to give Compound 23.

Workup

concentrationThe mixture was concentrated
additionthe residue was diluted with H2O
washwashed with EtOAc
extractionextracted with EtOAc
washthe combined organic layers were washed with H2O and brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-5f191085416e444aa4a1e0db500acab5
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08049015B2

Reaction notes

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