2-Dimethylaminopyridine → N-(p-chlorophenyl)valine

HRID 903166Notes

Reaction equation

HRID 903166 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]C2=O)=[CH:4][CH:3]=1.CN(C1C=CC=CN=1)C.O(C1N=C(CO)C=CC=1)C1C=CC=CC=1>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C@H:12]([C:11]([OH:16])=[O:10])[CH:13]([CH3:15])[CH3:14])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 218852-DimethylaminopyridineHCID 128791556-Phenoxy-2-pyridinemethanolHCID 132294943-(4-Chlorophenyl)-4-isopropyloxazolidine-2,5-dione

Product 1

HCID 13796078N-(p-chlorophenyl)valine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-(4-chlorophenyl)-4-isopropyl-oxazolidine-2,5-dione (336 mg, 1.32 mmol) and dimethylaminopyridine in 5 ml of dry tetrahydrofuran is added a solution of (6-phenoxy-2-pyridyl)methanol (254 mg, 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, yellow liquid, is chromatographed on a rotary chromatograph eluting with 15% ether/hexane to give the (6-phenoxy-2-pyridyl)methyl ester of N-(4-chlorophenyl)valine, a colorless oil.

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, yellow liquid, is chromatographed on a rotary chromatograph
  7. washeluting with 15% ether/hexane

Sources & evidence

ORD record
ord-daaf4669c68d4fa1a53fb6d4550d01ad
Source dataset
uspto-grants-1980_10
Patent number
US04226872

Reaction notes

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