Lithium Hydroxide → 3-Cyclopentyl-2-(4-morpholin-4-yl-phenyl)-propionic acid

HRID 1935233Notes

Reaction equation

C[O:2][C:3](=[O:23])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[CH:13][CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Li+]>O1CCCC1>[CH:6]1([CH2:5][CH:4]([C:11]2[CH:12]=[CH:13][C:14]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[CH:15][CH:16]=2)[C:3]([OH:23])=[O:2])[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 3-cyclopentyl-2-(4-morpholin-4-yl-phenyl)-propionic acid methyl ester (210.8 mg, 0.66 mmol) in tetrahydrofuran (830 μL) was treated with a 0.8M aqueous lithium hydroxide solution (1.2 mL). The reaction mixture was stirred at 25° C. for 23 h and then concentrated in vacuo to remove tetrahydrofuran. The white residue was acidified to pH=2 with a 10% aqueous hydrochloric solution. The resulting aqueous phase was extracted with ethyl acetate (2×75 mL). The combined organic extracts were washed with a saturated aqueous sodium chloride solution (1×100 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Trituration from hexanes/diethyl ether afforded 3-cyclopentyl-2-(4-morpholin-4-yl-phenyl)-propionic acid (173.7 mg, 86%) as a white solid: mp 145-147° C.; EI-HRMS m/e calcd for C18H25NO3 (M+) 303.1834, found 303.1843.

Workup

concentrationconcentrated in vacuo
customto remove tetrahydrofuran
extractionThe resulting aqueous phase was extracted with ethyl acetate (2×75 mL)
washThe combined organic extracts were washed with a saturated aqueous sodium chloride solution (1×100 mL)
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-05741307988e4f1ab7a7f94f6b9f050e
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06384220B2

Reaction notes

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