p-Toluenesulfonic acid monohydrate → HCID 54136862, compound

HRID 1941331Notes

Reaction equation

HRID 1941331 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[C@H:5]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[O:31][N:30]=[CH:29][CH:28]=2)=[CH:23][CH:22]=1)[N:6]=C(C1C=CC=CC=1)C1C=CC=CC=1)[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(#N)C.O>[CH2:1]([O:3][C:4](=[O:32])[C@H:5]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[O:31][N:30]=[CH:29][CH:28]=2)=[CH:23][CH:22]=1)[NH2:6])[CH3:2]

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 86751784HCID 86751784, compound

Product 1

HCID 54136862HCID 54136862, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Crude (±)-N-diphenylmethylene-3-[4-(5-isoxazolyl)-phenyl]-alanine ethyl ester (280 mg) was treated with p-toluenesulfonic acid monohydrate (100 mg) in acetonitrile (35 ml) and water (3.5 ml) at ambient temperature for 3.5 hours. After concentration the residue is extracted with ether and 1N sodium hydroxide, washed with brine, dried, and concentrated to give crude 3-[4-(5-isoxazolyl)-phenyl]-alanine ethyl ester.

Workup

  1. concentrationAfter concentration the residue
  2. extractionis extracted with ether and 1N sodium hydroxide
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d94c92759305454fa2039d71f75bc6df
Source dataset
uspto-grants-1997_12
Patent number
US05703106

Reaction notes

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