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

HRID 1739447Notes

Reaction equation

HRID 1739447 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].O.C(=O)([O-])[O-].[K+:38].[K+]>CO>[K+:38].[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 3

HCID 962WaterHCID 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 1

HCID 887MethanolSolvent

Procedure

A 100 mg (0.23 mM) quantity the less polar isomer of (4S,5R)-N-(t-butylamino-carbonyl)-2-(2,4-dimethoxyphenyl)-4phenyl-5-oxazolidinecarboxylic acid methyl ester (Preparation 57, 5Ka) is stirred at room temperature under nitrogen in 3 mL MeOH. To this is added 0.1 mL water and 43 mg (0.31 mM) potassium carbonate. After 1 hour, TLC shows no starting material left. Store in freezer overnight. The next morning the solvent is evaporated to give (4S,5R)-N-(t-butylaminocarbonyl)-2-(2,4dimethoxyphenyl)-4phenyl-5-oxazolidine-carboxylic acid potassium salt (6Ka).

Workup

  1. waitleft
  2. waitStore in freezer overnight
  3. customThe next morning the solvent is evaporated

Sources & evidence

ORD record
ord-66ef6e00ead448cfadfe38113ff977e7
Source dataset
uspto-grants-1999_10
Patent number
US05965739

Reaction notes

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