Water → 153652-66-5

HRID 2303987Notes

Reaction equation

HRID 2303987 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@@H:11]([C:19]([O:21]C)=[O:20])[O:10][C@@H:9]1[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.C(=O)([O-])[O-].[K+].[K+]>CO>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@@H:11]([C:19]([OH:21])=[O:20])[O:10][C@@H:9]1[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 57084446HCID 57084446, compound

Product 1

HCID 57094035153652-66-5Yield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

33 mg (0.08 mmol) of (2R,4S,5S)-3-t-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-5-methoxycarbonyl-1,3-oxazolidine, in suspension in 15 cm3 of methanol, are put, under an argon atmosphere, into a 50 cm3 round-bottomed flask equipped with a magnetic stirrer system. 5 cm3 of water and 33 mg (0.24 mmol) of potassium carbonate are then added. The mixture is allowed to react for 96 hours at a temperature in the region of 25° C. The reaction mixture becomes homogeneous. The methanol is removed under reduced pressure. The basic aqueous phase is diluted in 10 cm3 of water and then extracted with 3 times 15 cm3 of ether. The aqueous phase is cooled to 0° C. and is then acidified, with vigorous stirring in the presence of 20 cm3 of dichloromethane, with a 4M aqueous hydrochloric acid solution to a pH of less than 1. The acidic aqueous phase is extracted 8 times with 20 cm3 dichloromethane. The combined organic phases are washed with 3 times 5 cm3 of water and then once with 5 cm3 of a saturated aqueous sodium chloride solution. The organic phases are dried over anhydrous sodium sulphate. After filtration and concentration to dryness under reduced pressure, there are obtained, with a yield of 94%, 30.0 mg (0.075 mmol) of (2R,4S,5S)-3-t-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid, the characteristics of which are the following:

Workup

  1. customequipped with a magnetic stirrer system
  2. customto react for 96 hours at a temperature in the region of 25° C
  3. customThe methanol is removed under reduced pressure
  4. additionThe basic aqueous phase is diluted in 10 cm3 of water
  5. extractionextracted with 3 times 15 cm3 of ether
  6. extractionThe acidic aqueous phase is extracted 8 times with 20 cm3 dichloromethane
  7. washThe combined organic phases are washed with 3 times 5 cm3 of water
  8. dry with materialThe organic phases are dried over anhydrous sodium sulphate
  9. filtrationAfter filtration and concentration to dryness under reduced pressure, there

Sources & evidence

ORD record
ord-dc8564f8113b419aa2fe179ce5aa6282
Source dataset
uspto-grants-2002_08
Patent number
US06433180B1

Reaction notes

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