Hydrochloric Acid → {4-Methoxy-3-[2-((4S,5R)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-ylmethyl)-4-trifluoromethyl-phenoxy]-phenyl}-acetic acid

HRID 885313Notes

Reaction equation

C([O:3][C:4](=[O:39])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][C:16]=2[CH2:25][N:26]2[C@@H:30]([CH3:31])[C@@H:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[O:28][C:27]2=[O:38])[CH:7]=1)C.[OH-].[Li+].Cl>CO>[CH3:13][O:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][C:4]([OH:39])=[O:3])=[CH:7][C:8]=1[O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:23])([F:24])[F:22])=[CH:17][C:16]=1[CH2:25][N:26]1[C@@H:30]([CH3:31])[C@@H:29]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[O:28][C:27]1=[O:38]

Participants

Conditions

Temperature: 60 °C

Procedure

To {4-methoxy-3-[2-((4S,5R)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-ylmethyl)-4-trifluoromethyl-phenoxy]-phenyl}-acetic acid ethyl ester (0.08 g, 0.15 mmol) in MeOH (4 mL) was added 1N aqueous lithium hydroxide (2 mL), and the reaction was stirred at 60° C. overnight. The mixture was acidified with 1N aqueous HCl, and the aqueous layer was extracted twice with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated, and the residue was purified by preparative HPLC to give the desired product.

Workup

extractionthe aqueous layer was extracted twice with EtOAc
dry with materialThe combined organic layers were dried over MgSO4
filtrationfiltered
concentrationconcentrated
customthe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-e097f3f6e7774d339b9640674411d533
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242145B2

Reaction notes

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