Hydrochloric Acid → (S)-2-[4-(4-methoxy-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-pentanoic acid

HRID 19069Notes

Reaction equation

C[O:2][C:3](=[O:24])[C@@H:4]([N:9]1[CH2:13][C:12]([O:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[CH:11][C:10]1=[O:23])[CH2:5][CH:6]([CH3:8])[CH3:7].O.[OH-].[Li+].Cl>O1CCCC1.O>[CH3:22][O:21][C:18]1[CH:17]=[CH:16][C:15]([O:14][C:12]2[CH2:13][N:9]([C@@H:4]([CH2:5][CH:6]([CH3:7])[CH3:8])[C:3]([OH:24])=[O:2])[C:10](=[O:23])[CH:11]=2)=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of (S)-2-[4-(4-methoxy-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-pentanoic acid methyl ester (0.38 g, 1.16 mmol) in tetrahydrofuran (8.75 mL) and water (2.9 mL) was treated with lithium hydroxide monohydrate (59 mg, 1.40 mmol). The reaction was stirred at 25° C. for 2.5 h. At this time, the reaction was diluted with water (50 mL), acidified with a 2N aqueous hydrochloric acid solution and then was extracted with 10% methanol/dichloromethane (3×75 mL). The combined organics were dried over sodium sulfate, filtered and concentrated in vacuo to afford (S)-2-[4-(4-methoxy-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-pentanoic acid (0.36 g, 99%) as a white solid: HR-ES-MS m/z calculated for C17H21NO5 [M+H]+ 320.1493, observed 320.1493. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.87 (d, J=6.5 Hz, 3H), 0.92 (d, J=6.5 Hz, 3H), 1.34-1.54 (m, 1H), 1.54-1.68 (m, 1H), 1.68-1.86 (m, 1H), 3.77 (s, 3H), 4.10 (d, J=18.1 Hz, 1H), 4.22 (d, J=18.1 Hz, 1H), 4.62 (dd, J=11.5, 4.2 Hz, 1H), 4.75 (s, 1H), 7.00 (d, J=9.1 Hz, 2H), 7.23 (d, J=9.1 Hz, 2H), 12.89 (br. s., 1H).

Workup

extractionwas extracted with 10% methanol/dichloromethane (3×75 mL)
dry with materialThe combined organics were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-ca8c2434b6d241488b59efaef6622b44
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741327B2

Reaction notes

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