[C:1]([CH:3]1[O:7]C(=O)[NH:5][C@@:4]1([CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:14][CH:13]=1)[CH3:9])#[CH:2].[OH-].[Na+].CCOC(C)=O.C([O-])(O)=O.[Na+]>C(O)C>[NH2:5][C:4]([CH3:9])([CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:16][CH:17]=1)[C@H:3]([OH:7])[C:1]#[CH:2]To a stirred solution of (R)-5-Ethynyl-4-[2-(4-heptyloxy-phenyl)-ethyl]-4-methyl-oxazolidin-2-one in ethanol (1 ml) is added NaOH (1 ml, 1M aqueous solution). The mixture is heated at reflux temperature for 20 hours. The reaction mixture is then poured onto a biphasic mixture of AcOEt and NaHCO3 (saturated aqueous solution). The aqueous phase is extracted with AcOEt (3 times). The combined organic layers are dried (Na2SO4) and concentrated under reduced pressure. The product is purified by RP-HPLC (ZORBAX Extend C-18) eluting with 5%→95% CH3CN in H2O (+0.1% TFA) to give the title compound.
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