Hydrochloric Acid → HCID 54673875, compound

HRID 1810414Notes

Reaction equation

HRID 1810414 reaction equation
[CH2:1]([N:3]([CH2:9][C:10]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][C:11]=1[C:20]1[CH:25]=[C:24]([C@@H:26]([CH3:42])[C:27](N2[C@H](C)[C@H](C3C=CC=CC=3)OC2=O)=[O:28])[CH:23]=[CH:22][C:21]=1[O:43][CH3:44])[C:4]([CH:6]1[CH2:8][CH2:7]1)=[O:5])[CH3:2].[OH:45]O.[OH-].[Li+].Cl>C1COCC1.O>[CH:6]1([C:4]([N:3]([CH2:9][C:10]2[CH:15]=[C:14]([C:16]([F:17])([F:19])[F:18])[CH:13]=[CH:12][C:11]=2[C:20]2[C:21]([O:43][CH3:44])=[CH:22][CH:23]=[C:24]([C@@H:26]([CH3:42])[C:27]([OH:45])=[O:28])[CH:25]=2)[CH2:1][CH3:2])=[O:5])[CH2:8][CH2:7]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 54673874HCID 54673874, compound

Product 1

HCID 54673875HCID 54673875, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Cyclopropanecarboxylic acid ethyl-{2′-methoxy-5′-[(R)-1-methyl-2-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-2-oxo-ethyl]-4-trifluoromethyl-biphenyl-2-ylmethyl}-amide (0.011 g, 0.02 mmol) in THF (1 mL) and H2O (1 mL) was treated with hydrogen peroxide (30%; 0.004 mL, 0.04 mmol) and lithium hydroxide (0.002 g, 0.04 mmol), and the reaction was stirred overnight at room temperature. The mixture was acidified to pH 3-4 with 1N aqueous HCl and extracted three times with EtOAc. The combined organic layers were dried and concentrated to give the title compound. M+H is 450.

Workup

  1. extractionextracted three times with EtOAc
  2. customThe combined organic layers were dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d49b328fe0ec41089d30504a06f213f4
Source dataset
uspto-grants-2013_01
Patent number
US08362044B2

Reaction notes

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