Hydrochloric Acid → HCID 44188952, compound

HRID 885332Notes

Reaction equation

HRID 885332 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:13]=2[CH2:19][N:20]2[C@@H:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:23][O:22][C:21]2=[O:31])[CH:6]=1.[OH-].[Li+].Cl>C1COCC1>[Br:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][C:7]2[CH:6]=[C:5]([CH2:4][C:3]([OH:32])=[O:2])[CH:10]=[CH:9][CH:8]=2)=[C:13]([CH2:19][N:20]2[C@@H:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:23][O:22][C:21]2=[O:31])[CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58237599HCID 58237599, compound

Product 1

HCID 44188952HCID 44188952, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To {3-[4-bromo-2-((S)-2-oxo-4-phenyl-oxazolidin-3-ylmethyl)-phenoxy]-phenyl}-acetic acid methyl ester (0.043 g, 0.09 mmol) in THF (2 mL) was added 1N aqueous lithium hydroxide (2 mL), and the reaction was stirred at room temperature for 3 hours, until no starting material was seen by analytical LCMS. The mixture was acidified with 1N aqueous HCl and extracted three times with EtOAc, and the combined organic layers were dried and concentrated. The residue was purified by silica gel chromatography to give the desired product (0.027 g).

Workup

  1. extractionextracted three times with EtOAc
  2. customthe combined organic layers were dried
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-ed91e4aec19246ea8858b4474b9f79e1
Source dataset
uspto-grants-2012_08
Patent number
US08242145B2

Reaction notes

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