Sodium hydride → HCID 58237555, compound

HRID 885291Notes

Reaction equation

HRID 885291 reaction equation
[CH3:1][C@H:2]1[C@@H:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:5][C:4](=[O:13])[NH:3]1.[H-].[Na+].[CH2:16]([O:18][C:19](=[O:38])[CH2:20][C:21]1[CH:26]=[C:25]([O:27][C:28]2[CH:33]=[CH:32][C:31]([Br:34])=[CH:30][C:29]=2[CH2:35]Br)[CH:24]=[CH:23][C:22]=1[Cl:37])[CH3:17]>O1CCOCC1>[CH2:16]([O:18][C:19](=[O:38])[CH2:20][C:21]1[CH:26]=[C:25]([O:27][C:28]2[CH:33]=[CH:32][C:31]([Br:34])=[CH:30][C:29]=2[CH2:35][N:3]2[C@@H:2]([CH3:1])[C@@H:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[O:5][C:4]2=[O:13])[CH:24]=[CH:23][C:22]=1[Cl:37])[CH3:17]

Participants

5

Reactant 3

HCID 24758Sodium hydride2×HCID 8531614-Methyl-5-phenyl-2-oxazolidinone, (4S,5R)-2×HCID 58237429[5-(4-Bromo-2-bromomethyl-phenoxy)-2-chloro-phenyl]acetic acid ethyl ester

Product 1

HCID 58237555HCID 58237555, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(4S,5R)-(−)-4-Methyl-5-phenyl-2-oxazolidinone (0.062 g, 0.35 mmol) was added to a vial containing sodium hydride (60% in mineral oil; 0.015 g, 0.38 mmol) in 1,4-dioxane (10 mL). After stirring for 30 minutes at room temperature, the mixture was added to a vial containing [5-(4-bromo-2-bromomethyl-phenoxy)-2-chloro-phenyl]-acetic acid ethyl ester (0.15 g, 0.32 mmol) at 10° C. The reaction was stirred at room temperature overnight, and then additional (4S,5R)-(−)-4-methyl-5-phenyl-2-oxazolidinone (0.062 g, 0.35 mmol), pretreated with sodium hydride (60% in mineral oil; 0.015 g, 0.38 mmol), was added and the reaction was stirred overnight. Once no starting material was observed by analytical LCMS, the mixture was carried forward to the hydrolysis step.

Workup

  1. additionthe mixture was added to
  2. stirringThe reaction was stirred at room temperature overnight
  3. additionwas added
  4. stirringthe reaction was stirred overnight
  5. customthe mixture was carried forward to the hydrolysis step

Sources & evidence

ORD record
ord-667a3c9540664029a39fbe9f1dbf5271
Source dataset
uspto-grants-2012_08
Patent number
US08242145B2

Reaction notes

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