Phosgene → (S)-4-(4-Nitrobenzyl)oxazolidin-2-one

HRID 343892Notes

Reaction equation

HRID 343892 reaction equation
[NH2:1][C@@H:2]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)[CH2:3][OH:4].[OH-].[K+].[C:17](Cl)(Cl)=[O:18]>C1(C)C=CC=CC=1.O>[N+:12]([C:9]1[CH:10]=[CH:11][C:6]([CH2:5][C@H:2]2[CH2:3][O:4][C:17](=[O:18])[NH:1]2)=[CH:7][CH:8]=1)([O-:14])=[O:13]

Participants

6

Reactant 3

HCID 6371PhosgeneHCID 14797Potassium HydroxideHCID 10397777(S)-2-Amino-3-(4-nitrophenyl)propan-1-ol

Product 1

HCID 10353477(S)-4-(4-Nitrobenzyl)oxazolidin-2-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

The product from step (b) (4.9 g) was suspended in toluene, the suspension cooled to 0° C. and a solution of potassium hydroxide (7.0 g) in water (56 ml) added dropwise. A solution of phosgene (62.5 ml of a 12% w/v solution in toluene) was added dropwise to the resulting solution over 30 minutes and stirring continued for 1 hour. The mixture was extracted with ethyl acetate and the extracts washed with brine, dried and evaporated in vacuo to give a yellow oil. Crystallisation from ethyl acetate gave the desired product as pale yellow crystals (2.3 g).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe extracts washed with brine
  3. customdried
  4. customevaporated in vacuo
  5. customto give a yellow oil
  6. customCrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-1b5ac88db5674811a8bafcf4ea022511
Source dataset
uspto-grants-1999_01
Patent number
US05863935

Reaction notes

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