Water → HCID 86748224, compound

HRID 2379013Notes

Reaction equation

HRID 2379013 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][CH2:11][C@H:12]([CH:14]([CH3:16])[CH3:15])[N:13]=2)=[CH:5][CH:4]=1)=[O:2].[C:17]([C@@H:21]([C@H:23]([C:25]([O:27][CH3:28])=[O:26])[OH:24])O)([O:19][CH3:20])=[O:18].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH:14]([C@H:12]1[CH2:11][O:10][C:9]([C:6]2[CH:5]=[CH:4][C:3]([CH:1]3[O:24][C@@H:23]([C:25]([O:27][CH3:28])=[O:26])[C@H:21]([C:17]([O:19][CH3:20])=[O:18])[O:2]3)=[CH:8][CH:7]=2)=[N:13]1)([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 11851Dimethyl L-tartrateHCID 54342974HCID 54342974, compound

Product 1

HCID 86748224HCID 86748224, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 0.8 g of (S)-2-(4-formylphenyl)-4-isopropyl-2-oxazoline and 1 g of dimethyl L(+)-tartrate in 50 ml of toluene is treated with 0.1 g of toluene-4-sulphonic acid. The mixture is heated to boiling for 2.5 hours and the water formed is distilled off simultaneously. Then, 4 drops of triethylamine are added to the reaction mixture. After cooling the mixture is washed with 20 ml of 1N sodium hydrogen carbonate solution and twice with 20 ml of water each time, dried over sodium sulphate and concentrated. Chromatography of the residue on silica gel with toluene/ethyl acetate (vol. 1:1) and recrystallization from ethanol gives pure dimethyl (4R,5R)-2-(4-[(S)-4-isopropyl-2-oxazolinyl]phenyl)-1,3-dioxolane-4,5-dicarboxylate

Workup

  1. temperatureThe mixture is heated
  2. distillationis distilled off simultaneously
  3. additionThen, 4 drops of triethylamine are added to the reaction mixture
  4. temperatureAfter cooling the mixture
  5. washis washed with 20 ml of 1N sodium hydrogen carbonate solution and twice with 20 ml of water each time
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated
  8. customChromatography of the residue on silica gel with toluene/ethyl acetate (vol. 1:1) and recrystallization from ethanol

Sources & evidence

ORD record
ord-e66148c2bb93462aa99aedbe8bf572c7
Source dataset
uspto-grants-1994_11
Patent number
US05360577

Reaction notes

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