3-(4-Chlorophenyl)-4-isopropyloxazolidine-2,5-dione → 3-Benzylpyrrolylmethyl 2-(4-chlorophenylamino)-3-methylbutanoate

HRID 1413969Notes

Reaction equation

HRID 1413969 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]([CH:13]([CH3:15])[CH3:14])[C:11](=[O:16])[O:10][C:9]2=O)=[CH:4][CH:3]=1.[CH2:18]([C:25]1[CH:29]=[CH:28][NH:27][C:26]=1CO)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C1C=CN=CC=1.O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:12]([CH:13]([CH3:15])[CH3:14])[C:11]([O:10][CH2:9][C:26]2[NH:27][CH:28]=[CH:29][C:25]=2[CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:16])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 132294943-(4-Chlorophenyl)-4-isopropyloxazolidine-2,5-dioneHCID 543430813-Benzyl-1-pyrrolylmethanol

Product 1

HCID 202893053-Benzylpyrrolylmethyl 2-(4-chlorophenylamino)-3-methylbutanoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-(4-chlorophenyl)-4-isopropyloxazolidine-2,5-dione (336 mg, 1.32 mmol) and 4-dimethylaminopyridine in 5 ml of dry tetrahydrofuran is added a solution of 3-benzylpyrrolylmethyl alcohol (1.26 mmol) in 3 ml of dry tetrahydrofuran. The reaction mixture is stirred for about 20 hours, under dry air, and then diluted with ether followed by washing with saturated aqueous sodium bicarbonate, water and saturated aqueous sodium chloride. After drying over calcium sulfate, solvent is evaporated. The crude product is chromatographed on a rotary chromatograph eluting with 15% ether/hexane to give 3-benzylpyrrolylmethyl 2-(4-chlorophenylamino)-3-methylbutanoate.

Workup

  1. customunder dry air
  2. additiondiluted with ether
  3. washby washing with saturated aqueous sodium bicarbonate, water and saturated aqueous sodium chloride
  4. dry with materialAfter drying over calcium sulfate, solvent
  5. customis evaporated
  6. customThe crude product is chromatographed on a rotary chromatograph
  7. washeluting with 15% ether/hexane

Sources & evidence

ORD record
ord-db062ecfb85846a4b9ba7ce355641982
Source dataset
uspto-grants-1981_02
Patent number
US04252724

Reaction notes

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