Hydrochloric Acid → (S)-3-cyclopentyl-2-(4-methoxy-2-oxo-2,5-dihydro-pyrrol-1-yl)-propionic acid

HRID 18950

Reaction equation

C[O:2][C:3](=[O:19])[C@@H:4]([N:11]1[CH2:15][C:14]([O:16][CH3:17])=[CH:13][C:12]1=[O:18])[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.O.[OH-].[Li+].Cl>O1CCCC1.O>[CH:6]1([CH2:5][C@H:4]([N:11]2[CH2:15][C:14]([O:16][CH3:17])=[CH:13][C:12]2=[O:18])[C:3]([OH:19])=[O:2])[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution containing (S)-3-cyclopentyl-2-(4-methoxy-2-oxo-2,5-dihydro-pyrrol-1-yl)-propionic acid methyl ester (1.42 g, 5.20 mmol) in tetrahydrofuran (10 mL) was treated with an aqueous solution of lithium hydroxide monohydrate (273 mg, 6.4 mmol) in water (10 mL). The mixture was stirred at 25° C. for 2.5 h, it was then acidified with 2N aqueous hydrochloric acid. The mixture was extracted with dichloromethane (2×30 mL). The combined organic layers was dried over magnesium sulfate and concentrated to afford (S)-3-cyclopentyl-2-(4-methoxy-2-oxo-2,5-dihydro-pyrrol-1-yl)-propionic acid, (855 mg, 65%), as an off-white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.08 (m, 2H), 1.36-1.88 (m, 9H), 3.78 (s, 3H), 3.95 (J=17.7 Hz, 2H), 4.54 (dd, J=4.5 Hz, 11.0 Hz, 1H), 5.16 (s 1H), 12.80 (s, 1H).

Workup

extractionThe mixture was extracted with dichloromethane (2×30 mL)
dry with materialThe combined organic layers was dried over magnesium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-20c64ddd147f4b89aa4a9d5b75f1c697
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741327B2

Linked notes

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