HCID 66892217, compound → HCID 66890151, compound

HRID 456220Notes

Reaction equation

HRID 456220 reaction equation
C([O:3][C:4](=[O:38])[CH2:5][C:6]1[CH:7]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:15]=2[CH2:24][N:25]2[C@@H:29]([CH3:30])[C@@H:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[O:27][C:26]2=[O:37])[C:9]([O:12]C)=[CH:10][CH:11]=1)C>Br.C(O)(=O)C>[OH:12][C:9]1[C:8]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:21])([F:22])[F:23])=[CH:16][C:15]=2[CH2:24][N:25]2[C@@H:29]([CH3:30])[C@@H:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[O:27][C:26]2=[O:37])=[CH:7][C:6]([CH2:5][C:4]([OH:38])=[O:3])=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 66892217HCID 66892217, compound

Product 1

HCID 66890151HCID 66890151, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

A solution of [6-methoxy-2′-((4S,5R)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-ylmethyl)-4′-trifluoromethyl-biphenyl-3-yl]-acetic acid ethyl ester (0.740 g, 1.41 mmol) in hydrogen bromide (3 mL) and acetic acid (3 mL) was stirred at 100° C. overnight. The mixture was partitioned between EtOAc and H2O, and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated to give the title compound.

Workup

  1. customThe mixture was partitioned between EtOAc and H2O
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-34611225b3604cc68cccc5bf8d4bb726
Source dataset
uspto-grants-2013_07
Patent number
US08497381B2

Reaction notes

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