C([O:4][CH2:5][CH2:6][C@:7]([OH:49])([C@@H:11]([C:29](=[O:48])[NH:30][C@H:31]([C:44]([O:46]C)=[O:45])[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][CH2:40][C:41]#[C:42][CH3:43])=[CH:35][CH:34]=1)/[CH:12]=[CH:13]/[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20](=[O:28])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:8]([OH:10])=[O:9])(=O)C.[Li+].[OH-]>CO>[CH2:40]([O:39][C:36]1[CH:37]=[CH:38][C:33]([CH2:32][C@H:31]([NH:30][C:29]([C@@H:11](/[CH:12]=[CH:13]/[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20](=[O:28])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C@@:7]([OH:49])([CH2:6][CH2:5][OH:4])[C:8]([OH:10])=[O:9])=[O:48])[C:44]([OH:46])=[O:45])=[CH:34][CH:35]=1)[C:41]#[C:42][CH3:43]No. 5214354, (E)-(2S,3S)-2-(2-acetoxy-ethyl)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2-hydroxy-12-oxo-nonadec-4-enoic acid (120 mg, 0.175 mmol) was dissolved in methanol (10 mL), and an aqueous solution (1 mL) of 2 M LiOH was added, and the mixture was stirred at room temperature. After confirming the consumption of the starting materials by LCMS, methanol was distilled off under reduced pressure. To the residue was added 1 M hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated brine and then dried over anhydrous sodium sulfate. The filtrate was concentrated under reduced pressure. The resulting residue was purified by preparative HPLC and freeze-dried to obtain the title compound (20 mg, 18% yield, white powder).
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