Potassium Carbonate → (4S,5R)-N-(t-butylaminocarbonyl)-2-(2,4dimethoxyphenyl)-4phenyl-5-oxazolidine-carboxylic acid potassium salt

HRID 567417Notes

Reaction equation

HRID 567417 reaction equation
C[O:2][C:3]([C@@H:5]1[O:9][CH:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=2[O:18][CH3:19])[N:7]([C:20]([NH:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C@H:6]1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:4].C(=O)([O-])[O-].[K+:37].[K+]>CO.O>[K+:37].[C:23]([NH:22][C:20]([N:7]1[C@@H:6]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C@H:5]([C:3]([O-:4])=[O:2])[O:9][CH:8]1[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=1[O:18][CH3:19])=[O:21])([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 53753692(4S,5R)-N-(t-Butylaminocarbonyl)-2-(2,4-dimethoxyphenyl)-4-phenyl-5-oxazolidinecarboxylic acid methyl ester

Product 1

HCID 69748715(4S,5R)-N-(t-butylaminocarbonyl)-2-(2,4dimethoxyphenyl)-4phenyl-5-oxazolidine-carboxylic acid potassium salt

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

(4S,5R)-N-(t-Butylaminocarbonyl)-2-(2,4dimethoxyphenyl)-4-phenyl-5-oxazolidinecarboxylic acid methyl ester (PREPARATION 2—less polar isomer, 6.27 g, 14.2 mM) is stirred at 20-25° under nitrogen in methanol (50 mL). To this mixture is added a solution of potassium carbonate (2.50 g, 18.1 mM) in water (6 mL). After 6 hr the reaction is concentrated under reduced pressure to remove the methanol and the residue freeze dried to give the title compound (admixed with potassium carbonate salts as a powder), NMR (DMSO-d6, TMS) 1.10, 3.77, 4.17, 4.70, 5.16, 6.50, 6.60 and 7.14-7.42 δ.

Workup

  1. concentrationAfter 6 hr the reaction is concentrated under reduced pressure
  2. customto remove the methanol
  3. customthe residue freeze dried

Sources & evidence

ORD record
ord-c2eee1e4be9749f694dd41f810cc39c8
Source dataset
uspto-grants-2001_01
Patent number
US06177573B1

Reaction notes

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