Lithium Hydroxide → (R)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-hexanoic acid

HRID 19412Notes

Reaction equation

C([O:3][C:4](=[O:25])[C@H:5]([N:11]1[CH2:15][C:14]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])=[CH:13][C:12]1=[O:24])[CH2:6][CH:7]([CH3:10])[CH2:8][CH3:9])C.[OH-].[Li+]>O1CCCC1>[Cl:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[O:16][C:14]1[CH2:15][N:11]([C@H:5]([CH2:6][CH:7]([CH3:10])[CH2:8][CH3:9])[C:4]([OH:25])=[O:3])[C:12](=[O:24])[CH:13]=1

Participants

Conditions

Temperature: 5 °C

Procedure

A solution of (R)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-hexanoic acid ethyl ester (1.25 g, 3.42 mmol) in tetrahydrofuran (14 mL) was treated with a 0.5N lithium hydroxide solution (4 mL) and stirred at 5° C. for 2 h. The mixture was concentrated in vacuo and the residue was dissolved in water (40 mL) and washed with diethyl ether. The organic phase was discarded and the aqueous layer acidified with 1N aqueous hydrochloric acid (10 mL) and extracted with ethyl acetate. The combined ethyl acetate layers were concentrated in vacuo which afforded (R)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-hexanoic acid (1.13 g, 98%) as a pale brown solid.

Workup

concentrationThe mixture was concentrated in vacuo
dissolutionthe residue was dissolved in water (40 mL)
washwashed with diethyl ether
extractionextracted with ethyl acetate
concentrationThe combined ethyl acetate layers were concentrated in vacuo which

Sources & evidence

ORD record: ord-22b8b902fbc346e48fdc89b7741c4918
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741327B2

Reaction notes

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